Synthesis and crystal structure determination of a new 1D polymer adduct of 1,2-di(pyridin-4-yl)ethane, based on B-N dative bonded eight-membered cyclo-1,3,3,5,7,7-hexaphenyl-1,5-dibora-3,7-disiloxane European Journal of Chemistry 15 (4) (2024) 325-331 European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2024 The Authors – Atlanta Publishing House LLC – Printed in the USA. This work is published and licensed by Atlanta Publishing House LLC – CC BY NC – Some Rights Reserved. https://dx.doi.org/10.5155/eurjchem.15.4.325-331.2597 European Journal of Chemistry View Journal Online View Article Online Synthesis and crystal structure determination of a new 1D polymer adduct of 1,2-di(pyridin-4-yl)ethane, based on B-N dative bonded eight-membered cyclo-1,3,3,5,7,7-hexaphenyl-1,5-dibora-3,7-disiloxane Okpara Sergeant Bull * and Chioma Don-Lawson Department of Chemistry, Rivers State University, Nkpolu-Oroworukwo, Port Harcourt, PMB 5080, Nigeria * Corresponding author at: Department of Chemistry, Rivers State University, Nkpolu-Oroworukwo, Port Harcourt, PMB 5080, Nigeria. e-mail: bull.okpara@ust.edu.ng (O.S. Bull). 10.5155/eurjchem.15.4.325-331.2597 Received: 19 September 2024 Received in revised form: 8 November 2024 Accepted: 10 November 2024 Published online: 31 December 2024 Printed: 31 December 2024 A novel 1D polymer of 1,2-di(pyridin-4-yl)ethane (L1), connected via B-N dative-bonded adduct with an eight-membered cyclo-1,3,3,5,7,7-hexaphenyl-1,5-dibora-3,7-disiloxane [Ph6B2Si2O4]·L1 was synthesized and characterized. The new compound [Ph6B2Si2O4]·L1 was prepared by the reaction of cyclo-1,3,3,5,7,7-hexaphenyl-1,5-dibora-3,7-disiloxane and bis(pyridyl)ethane in a mixture of diethyl ether and petroleum ether solvents at reflux. The 1D polymer [Ph6B2Si2O4]·L1 was characterized by single-crystal X-ray diffraction, nuclear magnetic resonance, and FT-IR spectroscopy. The single crystal X-ray diffraction studies reveal that the aforementioned compound crystalized in the monoclinic crystal system with a centrosymmetric space group of P21/n (no. 14), a = 16.5378(4) Å, b = 12.6201(3) Å, c = 20.4904(5) Å, β = 96.689(2)°, V = 4247.43(18) Å3, Z = 4, T = 173.0 K, μ(MoKα) = 0.130 mm-1, Dcalc = 1.233 g/cm3, 14630 reflections measured (4.96° ≤ 2Θ ≤ 56.424°), 8424 unique (Rint = 0.0235, Rsigma = 0.0460) which were used in all calculations, the final R1 was 0.0455 (I > 2σ(I)) and wR2 was 0.1201 (all data). Furthermore, the compound exhibits various noncovalent interactions in the crystal packing, such as intermolecular and intramolecular, as well as hydrogen bonding. This study demonstrates the potential for making novel materials via the combination of cyclodiboradisiloxanes (Lewis acid) and nitrogen- containing ligands (Lewis bases). 1D polymer Diphenylsilanediol Phenylboronic acid Cyclodiboradisiloxane 1,2-Di(pyridin-4-yl)ethane B-N dative-bonded-adduct Cite this: Eur. J. Chem. 2024, 15(4), 325-331 Journal website: www.eurjchem.com 1. Introduction In recent decades, cyclodiboradisiloxanes and their derivatives as a class of organoborasilicon compounds have garnered great attention due to their exceptional structural architecture, magnetic properties, electronic properties, optical properties, quasiaromatic character, as well as their aptitude for the formation of extended intramolecular and inter- molecular interactions [1]. These groups of compounds consist of mainly alkyl Si-O-B and O-B-O ring systems in which the boron centres (if tricoordinated) are further ligated with Lewis bases such as pyridines, phosphines, carboxylates, ethers, aryl- sulphides, thioethers, imines, oximes etc. leading to the formation of B-N, B-P, B-O, B-S and so forth dative bonds, which imparts remarkable stability and reactivity. The presence of silicon and oxygen atoms within the cyclodiboradisiloxane affords the framework with unusual high elasticity and plasticity when subjected to sudden and slow stress. Boron- nitrogen adducts, which as those formed between cyclo- diboradisiloxanes and nitrogen-containing ligands, have shown great potential applications in various fields, such as: conductive polymers for advanced energy devices, catalysis, carbon capture, gas separation, and adsorption, lightweight, high-strength materials for application in spacecraft, pharmaceuticals, and drug delivery. The ability to form stable covalent bonds between boron and nitrogen atoms enables the creation of novel materials with tailored properties. Further- more, polymers, in particular, have revolutionized modern technology, finding applications in everything from packaging materials to advanced electronics. The development of novel polymers with unique properties, such as conductivity, luminescence, or stimulus responsiveness, is an active area of research [2]. The incorporation of cyclodiboradisiloxanes and boron-nitrogen adducts into polymer backbones or side chains offers a promising route to the preparation of materials with enhanced performance and functionality [3-10]. Regardless of the functions and uses of these borasiloxane materials, as well as their promising future prospects, only a few of these materials are available in the literature [4,11-15]. This dearth of literature and materials could be due to the availability of a handful of commercially available silanols, difficulties in structural modification of available materials, and problems of stability. The methods for the preparation of these materials are discussed in detail in the literature [4,7,14,16]. However, the method used in this study is similar to that described in the literature [4], in which molecular sieves were used to remove ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.15.4.325-331.2597 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.15.4.325-331.2597 mailto:bull.okpara@ust.edu.ng http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.15.4.325-331.2597&domain=pdf&date_stamp=2024-12-31 326 Bull and Don-Lawson / European Journal of Chemistry 15 (4) (2024) 325-331 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.4.325-331.2597 Table 1. Crystal data and structure refinement for [Ph6B2Si2O4]·L1 (5). Empirical formula C48H42B2N2O4Si2 Formula weight (g/mol) 788.63 Temperature (K) 173.0 Crystal system Monoclinic Space group P21/n a, (Å) 16.5378(4) b, (Å) 12.6201(3) c, (Å) 20.4904(5) α (°) 90 β (°) 96.689(2) γ (°) 90 Volume (Å3) 4247.43(18) Z 4 ρcalc (g/cm3) 1.233 μ (mm-1) 0.130 F(000) 1656.0 Crystal size (mm3) 0.6 × 0.32 × 0.18 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 4.96 to 56.424 Index ranges -21 ≤ h ≤ 14, -16 ≤ k ≤ 15, -26 ≤ l ≤ 21 Reflections collected 14630 Independent reflections 8424 [Rint = 0.0235, Rsigma = 0.0460] Data/restraints/parameters 8424/0/523 Goodness-of-fit on F2 1.025 Final R indexes [I≥2σ (I)] R1 = 0.0455, wR2 = 0.1070 Final R indexes [all data] R1 = 0.0682, wR2 = 0.1201 Largest diff. peak/hole (e.Å-3) 0.77/-0.29 Scheme 1. Synthesis of (Ph6B2Si2O4) (3) and [Ph6B2Si2O4]·L1 (5) adduct polymer. water, as shown in Scheme 1, to obtain the crude compound 3. Compound 3 (Lewis acid) was ligated with 1,2-di(pyridin-4- yl)ethane (L1) leading to the formation of the aforementioned 1D polymer (5) following a literature procedure [4]. Therefore, the main purpose of the study was to synthesize and determine the crystal structure of a new 1D polymer adduct of 1,2- di(pyridin-4-yl)ethane, based on B-N dative bonded eight- membered cyclo-1, 3, 3, 5, 7, 7-hexaphenyl-1, 5-dibora-3, 7- disiloxane (Ph6B2Si2O4) (3) as shown in Scheme 1. 2. Experimental 2.1. Chemicals and reagents All chemicals, reagents, and solvents were purchased from Sigma-Aldrich or Alfa-Aesar and used as received unless otherwise stated. Molecular sieves (1.6 mm rods and 0.4 nm pores) were preheated to dryness in the oven at 120 °C for two weeks prior to use. 2.2. Instrumentation 1H, 13C{1H}, 11B{1H}, and 29Si{1H} NMR spectra were recorded on Bruker AVANCE III HD 400 MHz or 500 MHz spectrometers in CDCl3 solvent unless otherwise stated. The chemical shifts (δ) for 1H and 13C{1H}, 29Si{1H}, and 11B{1H}, are quoted in ppm with reference to Me4Si and BF3OEt2, respectively. Coupling constants are reported in Hz. Infrared spectra were obtained on a Perkin Elmer Spectrum 100 FTIR Spectrometer operating in ATR mode. 2.3. Synthesis 2.3.1. Synthesis of Ph6B2Si2O4 In a round bottom flask equipped with a magnetic stirrer bar, diphenylsilanediol (1) (1.082 g, 5.0 mmol) was mixed with 0.609 g (5.0 mmol) of phenylboronic acid (2) in dry toluene (50 mL) and 0.5 g of molecular sieves. Bull and Don-Lawson / European Journal of Chemistry 15 (4) (2024) 325-331 327 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.4.325-331.2597 Figure 1. 1-D polymeric structure of compound [Ph6B2Si2O4]·L2 (5). Colour identity, Yellow = B, orange = Si, grey = C, blue = N, red= O and white = H. The mixture was refluxed under N2 for 20 h. Thereafter, the round bottom flask and its contents were allowed to cool to room temperature. The mixture was filtered, and the filtrate was collected. The molecular sieves were washed with dry toluene (3 × 25 mL) followed by filtraton and collection of the filtrate. The filtrates were combined and concentrated under reduced pressure and the solid residue was recrystallized from diethyl ether and petroleum ether (3:1 ratio) to give compound 3. Cyclo-1,3,3,5,7,7-hexaphenyl-1,5-dibora-3,7-disiloxane (3): Colour: White. Yield: 1.30 g, 86%. M.p.: 162.0-163.0 °C (Lit. 161- 162 °C [17]). 1H NMR (500 MHz, CDCl3, δ, ppm): 7.31-7.54 (m, 18H, m, p-C6H5), 7.73-7.75 (m, 8H o-C6H5Si), 8.08-8.10 (m, 4H, o-C6H5B). 13C NMR (125 MHz, CDCl3, δ, ppm): 127.93, 128.06, 130.60, 131.74, 133.40, 134.12, 135.65 (C6H5Si, C6H5B). 11B NMR (160 MHz, CDCl3, δ, ppm): 25.69. 29Si{1H} NMR (99 MHz, CDCl3, δ, ppm): -45.00. MS (70 eV, EI, m/z): 604 (M+), 527 (M- Ph)+, 423 (M-Ph-PhBO)+, 406 (M-Ph2SiO)+. FT-IR (ATR, ν, cm-1): 3023 (C-HAr.), 1349 (B-O), 1307 (Si-C str.), 1071 (Si-O str.). 2.3.2. Synthesis of [Ph6B2Si2O4]·L1 In a round bottom flask, [Ph6B2Si2O4] (3) (0.125 g, 0.208 mmol) was dissolved in ether (20 mL) and stirred with a magnetic stirrer bar. In another round bottom flask, 1,2-bis (pyridyl)ethane (L1) (0.038 g, 0.208 mmol) was dissolved in ether (20 mL) and stirred. The [Ph6B2Si2O4] solution was added to 1,2-bis(pyridyl)ethane while stirring. The reaction mixture was stirred for 24 h during which time a milky solution formed. The removal of ether via filtration yielded a colourless powder. Recrystallisation from CH2Cl2:ether (2:1, v:v) through slow evaporation gave colourless crystals after 24 h of [Ph6B2Si2O4]·L1 (5). Colour: White. Yield: 0.14 g, 87%. M.p.: 196- 197 °C. 1H NMR (500 MHz, CDCl3, δ, ppm): 2.94 (s, 4H, CH2CH2), 7.09-7.10 (m, 4H, m-C5H4N), 7.31-7.49 (m, 18H, m, p-C6H5), 7.68-7.70 (m, 8H, o-C6H5Si), 8.02-8.04 (m, 4H, o-C6H5B), 8.55-8.56 (m, 4H, o-C5H4N). 13C NMR (125 MHz, CDCl3, δ, ppm): 150.64, 148.36, 135.27, 134.32, 134.12, 133.88, 133.59, 131.17, 130.33, 127.90, 127.79, 127.51, 124.06, 33.52. 11B{1H}, NMR: δ (CDCl3, 160 MHz): 19.86. 29Si{1H}, NMR: δ (CDCl3, 99 MHz): - 45.60. FT-IR (KBr, ν, cm-1): 3017 (C-H Ar), 1477 (CH2 scissor), 1412 (B-O), 1379 (C-N), 1251 (CH2 rock), 1114 (CH2 wag), 1073 (Si-O). 3. Results and discussion Cyclo-1, 3, 3, 5, 7,7 -hexaphenyl-1, 5-dibora-3, 7-disiloxane (Ph6B2Si2O4) (3) was obtained as colourless crystalline solids and readily soluble in nonpolar organic solvents such as benzene and hexane. Compound 3 was characterized using standard analytical and spectroscopic methods. The 1H NMR spectrum of compound 3 showed well-resolved resonances for which aromatic proton signals were found within the range of δ 7.31-8.10 ppm, and this range of values is comparable to the values reported in the literature [4,11,17,18]. Furthermore, the 13C{1H} NMR spectrum of compound 3 showed signals for the aromatic carbon atoms in the range of δ 127.93-135.65 ppm, these are also in accordance with the values reported in the literature [4,11,17,18]. The 11B{1H} NMR of compound 3 showed a broad singlet at δ 25.69 ppm. This value is symbolic of a single boron chemical environment. Furthermore, the 29Si NMR of compound 3 showed a singlet at δ -45.00 ppm. Furthermore, the IR spectrum obtained from compound 3 showed strong absorption peaks in the regions: ν(cm-1) 3023, C-H aromatic; 1349, B-O; 1307, Si-C; and 1071 for Si-O stretching mode [4,19]. Subsequently, compound 3 was treated with a 1,2-bis(pyridyl) ethane ligand to give compound 5. The 11B{1H} NMR and 29Si{1H} NMR spectra of compound 5 showed singlets at δ 19.86 and -45.60 ppm, respectively. Data obtained through single crystal X-ray diffraction studies reveal that compound 5 comprises the eight-membered ring structure, (i.e. compound 3), and linker L1 (i.e. 1,2-di(pyridin-4-yl)ethane) as shown in Figure 1. Compound 5 crystallized in the monoclinic crystal system with a centrosymmetric space group of P21/n, as shown in Table 1, while the bond lengths and angles are shown in Table 2. As shown in Figure 1, the two B atoms are tetracoordinate. Each boron atom is bonded to two O atoms, one C atom from a phenyl ring, and one N via a coordination (dative bond) to the 1,2-di(pyridin-4-yl)ethane (L1) to give a 1-D polymeric structure compound 5. The B-O-Si angles of compound 5 range from 133.24(12) to 143.93(13)° with an average value of 139.69(13)°, which are comparable to those of compound [4], and show distortion at the O atoms in the ring as revealed in the ellipsoid plot Figure 2, compared to compound 3. The four B-O distances in compound 5 range from 1.321(2) to 1.442(3) Å with a mean value of 1.436 Å. These B-O bond distances are longer than the B-O length for a tricoordinated B in Si2B2O4 rings, which range from (1.36-1.39 Å) [11,19,20] but similar to those of the compound reported in the literature [4] discussed earlier. The longer bond length observed at the tetrahedrally bonded B site compared to the tricoordinated B may be linked to a reduction in the B-O π-bonding component on changing from trigonal to tetrahedral coordination geometry at the B atom. Furthermore, the four lengths of Si-O bonds in compound 5 range from 1.604(14) to 1.618(13) Å, which are similar to those found in compound in the literature [4,21-23]. 328 Bull and Don-Lawson / European Journal of Chemistry 15 (4) (2024) 325-331 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.4.325-331.2597 Table 2. Bond lengths and bond angles of [Ph6B2Si2O4]·L1 (5). Atom Atom Length (Å) Atom Atom Length (Å) B1 O2 1.442(3) C24 C25 1.380(3) B1 O8 1.431(2) C25 C26 1.382(4) B1 N9 1.671(3) C26 C27 1.366(4) B1 C23 1.608(3) C27 C28 1.384(3) O2 Si3 1.6057(14) C29 C30 1.397(3) Si3 O4 1.6085(13) C29 C34 1.394(3) Si3 C29 1.871(2) C30 C31 1.390(3) Si3 C35 1.866(2) C31 C32 1.364(4) O4 B5 1.437(3) C32 C33 1.376(4) B5 O6 1.432(2) C33 C34 1.382(3) B5 N201 1.702(3) C35 C36 1.397(3) B5 C41 1.603(3) C35 C40 1.392(3) O6 Si7 1.6035(14) C36 C37 1.381(3) Si7 O8 1.6047(14) C37 C38 1.367(4) Si7 C47 1.868(2) C38 C39 1.388(4) Si7 C53 1.8689(19) C39 C40 1.384(3) N9 C10 1.337(3) C41 C42 1.388(3) N9 C14 1.335(2) C41 C46 1.389(3) C10 C11 1.374(3) C42 C43 1.388(3) C11 C12 1.384(3) C43 C44 1.380(3) C12 C13 1.381(3) C44 C45 1.375(3) C12 C15 1.508(3) C45 C46 1.388(3) C13 C14 1.368(3) C47 C48 1.389(3) C15 C16 1.508(3) C47 C52 1.391(3) C16 C17 1.505(3) C48 C49 1.387(3) C17 C18 1.378(3) C49 C50 1.368(4) C17 C22 1.385(3) C50 C51 1.376(4) C18 C19 1.374(3) C51 C52 1.387(3) C19 N20 1.339(3) C53 C54 1.392(3) N20 B52 1.702(3) C53 C58 1.393(3) N20 C21 1.332(3) C54 C55 1.386(3) C21 C22 1.379(3) C55 C56 1.376(3) C23 C24 1.388(3) C56 C57 1.372(3) C23 C28 1.392(3) C57 C58 1.388(3) Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) O2 B1 N9 103.26(15) C19 N20 B52 121.11(16) O2 B1 C23 116.02(17) C21 N20 B52 120.79(16) O8 B1 O2 115.78(17) C21 N20 C19 118.08(17) O8 B1 N9 105.17(15) N20 C21 C22 122.3(2) O8 B1 C23 110.21(16) C21 C22 C17 120.2(2) C23 B1 N9 104.89(15) C24 C23 B1 119.84(19) B1 O2 Si3 141.00(12) C24 C23 C28 116.3(2) O2 Si3 O4 114.88(7) C28 C23 B1 123.85(19) O2 Si3 C29 109.82(8) C25 C24 C23 122.4(2) O2 Si3 C35 108.10(9) C24 C25 C26 119.6(3) O4 Si3 C29 105.63(8) C27 C26 C25 119.5(2) O4 Si3 C35 110.74(8) C26 C27 C28 120.3(2) C35 Si3 C29 107.43(9) C27 C28 C23 121.8(2) B5 O4 Si3 133.24(12) C30 C29 Si3 120.77(17) O4 B5 N201 101.82(15) C34 C29 Si3 122.33(16) O4 B5 C41 114.24(17) C34 C29 C30 116.9(2) O6 B5 O4 115.49(16) C31 C30 C29 121.5(2) O6 B5 N201 107.20(15) C32 C31 C30 119.9(2) O6 B5 C41 111.22(17) C31 C32 C33 120.2(2) C41 B5 N201 105.67(14) C32 C33 C34 120.1(2) B5 O6 Si7 143.93(13) C33 C34 C29 121.4(2) O6 Si7 O8 113.07(7) C36 C35 Si3 122.31(17) O6 Si7 C47 109.47(8) C40 C35 Si3 120.53(16) O6 Si7 C53 106.46(8) C40 C35 C36 117.1(2) O8 Si7 C47 104.60(8) C37 C36 C35 121.2(2) O8 Si7 C53 111.75(8) C38 C37 C36 120.4(2) C47 Si7 C53 111.58(9) C37 C38 C39 120.1(2) B1 O8 Si7 140.58(13) C40 C39 C38 119.1(2) C10 N9 B1 121.11(16) C39 C40 C35 122.0(2) C14 N9 B1 120.53(16) C42 C41 B5 121.58(19) C14 N9 C10 118.07(17) C42 C41 C46 116.91(19) N9 C10 C11 122.2(2) C46 C41 B5 121.50(18) C10 C11 C12 120.1(2) C43 C42 C41 122.0(2) C11 C12 C15 122.2(2) C44 C43 C42 119.7(2) C13 C12 C11 116.86(19) C45 C44 C43 119.7(2) C13 C12 C15 120.9(2) C44 C45 C46 120.0(2) C14 C13 C12 120.3(2) C45 C46 C41 121.8(2) N9 C14 C13 122.4(2) C48 C47 Si7 122.74(15) C16 C15 C12 111.61(19) C48 C47 C52 116.96(19) C17 C16 C15 112.06(19) C52 C47 Si7 120.20(16) C18 C17 C16 121.3(2) C49 C48 C47 121.9(2) C18 C17 C22 116.75(19) C50 C49 C48 119.8(2) C22 C17 C16 121.9(2) C49 C50 C51 119.9(2) C19 C18 C17 120.5(2) C50 C51 C52 120.0(2) N20 C19 C18 122.2(2) C51 C52 C47 121.4(2) 1 -1/2+x, 1/2-y, 1/2+z; 2 1/2+x, 1/2-y, -1/2+z. Bull and Don-Lawson / European Journal of Chemistry 15 (4) (2024) 325-331 329 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.4.325-331.2597 Table 3. Hydrogen bonds and C-H⋅⋅⋅π contacts for compound 5. Donor-H···Acceptor D-H, Å H···A, Å D···A, Å D-H···A, ° Symmetry C10-H10A···O8 0.95 2.47 2.825(3) 102 - C14-H14A···O2 0.95 2.44 2.793(3) 102 - C21-H21A···O4 0.95 2.41 2.755(3) 101 1/2+x, 1/2-y, -1/2+z C46-H46A···O6 0.95 2.50 2.865(3) 103 - C–H⋅⋅⋅Cg a H⋅⋅⋅Cg, Å H-Perp b γ c ∠ C-H⋅⋅⋅Cg, ° C⋅⋅⋅Cg, Å Symmetry C13-H13A···Cg(5) 2.66 -2.62 10.17 137 3.414(2) 1-x, 1-y, 1-z C16-H16A···Cg(4) 2.80 2.68 17.11 169 3.777(3) 1-x, 1-y, 1-z a Cg: Center of gravity of ring J, Cg(5): C35/C40, Cg(4): C29/C34. b Perpendicular distance of H to the ring plane J. c Angle between Cg-H vector and ring J normal. Figure 2. An ORTEP diagram of [Ph6B2Si2O4]·L2 (5) with atom labelling. Colour identity, Yellow = B, orange = Si, grey = C, blue = N, red= O and white = H. Figure 3. Two polymer chains with C-H···π and C-H···O interactions in the crystal packing of compound 5. Colour identity, pink = B, ornge = Si, grey = C, blue = N, red= O and white = H. The B-N bond lengths in compound 5 are 1.671(3) Å and 1.702(3) Å with an average value of 1.686(3) Å. Just like compound [4], the B-N bond lengths for compound 5 are slightly longer than those of simple borosiloxane such as Ph(OSiR2Rˊ)B{OCH2)3N} [24] (R or Rˊ = Ph or CH3) and [ButSi(OPhBO)3SiBut]·NC5H5 [19]. The Si-C bond lengths in compound 5 range 1.866(2) to 1.871(2) Å with an average bond distance of 1.868(2) Å. The ring angles of O2-B1-O8 and O4-B5-O6 are 115.78(17)° and 115.49(16)°, respectively, with a mean value of 115.64(16)°. The mean internal ring angle of compound 5 is higher than 109.5° expected for a tetrahedral geometry but similar to compound [4] as well as the observation reported in the literature [19]. Similarly, the ring angles of silicon; O2-Si3- O4 and O6-Si7-O8 are 114.88(7)° and 113.07(7)°, respectively, with a mean value of 113.98(7)° which is also slightly higher than 109.5° for a tetrahedral silicon. The other bond angles of Si as well as the Si-C bond lengths are comparable to compounds [4] as well as other borasiloxane compounds and simple adducts in the literature [11,19,25]. Molecular interactions determine the supramolecular structure of the compound 5 (Table 3). In addition to the covalent and dative bonds found in compound 5, the crystal packing of the compound also shows noncovalent interactions C-H···π (2.80 Å) and C-H···O (2.44 Å) [26,27] as shown in Figure 3. These two interactions differ from those observed in similar compounds reported in the literature [4]. 330 Bull and Don-Lawson / European Journal of Chemistry 15 (4) (2024) 325-331 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.4.325-331.2597 4. Conclusions In this article, the successful synthesis and determination of the crystal structure of a new 1D polymer (5) adduct of 1,2- di(pyridin-4-yl)ethane (L1), based on an eight-membered cyclo- 1,3,3,5,7,7-hexaphenyl-1,5-dibora-3,7-disiloxane (Ph6B2Si2O4) (3) was reported here. The crystal structure of compound 5 was determined using single-crystal X-ray diffraction. The structure has intermolecular and intramolecular interactions. This novel 1D polymer has promising potential to enhance the performance and functionality of borasiloxane backbone materials. Therefore, further work is recommended to explore some functions and uses of this unique cyclo-1,3,3,5,7,7- hexaphenyl-1,5-dibora-3,7-disiloxane (Ph6B2Si2O4) (3) 1D B-N adduct polymer in areas such as heterogeneous catalyst in the conversion of cooking oil to biodiesel, adsorption of heavy metals from waste water, optoelectronic applications such as Organic Light-Emitting Diodes (OLEDs), Organic Photovoltaics (OPVs) and sensor, energy storage and conversion, biomedical and biotechnology etc. Acknowledgements We gratefully acknowledge the financial support given to us by the Nigerian Government through the Petroleum Technology Development Fund (PTDF), the Tertiary Education Trust Fund (TETFUND), and the Rivers State University, Port Harcourt, Nigeria. Supporting information CCDC-2403230 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033. Disclosure statement Conflict of interest: The authors declare that they have no conflict of interest. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compounds are available from the author. CRediT authorship contribution statement Conceptualization: Okpara Sergeant Bull; Conceptualization: Okpara Sergeant Bull; Methodology: Okpara Sergeant Bull; Software: Okpara Sergeant Bull; Validation: Chioma Don-Lawson, Okpara Sergeant Bull; Formal Analysis: Okpara Sergeant Bull; Investigation: Okpara Sergeant Bull; Resources: Chioma Don-Lawson; Data Curation: Okpara Sergeant Bull; Writing - Original Draft: Okpara Sergeant Bull; Writing - Review and Editing: Okpara Sergeant Bull, Chioma Don-Lawson; Visualization: Chioma Don- Lawson; Funding acquisition: Chioma Don-Lawson; Supervision: Chioma Don-Lawson; Project Administration: Okpara Sergeant Bull. ORCID and Email Okpara Sergeant Bull bull.okpara@ust.edu.ng https://orcid.org/0000-0002-5810-1483 Chioma Don-Lawson chioma.don-lawson@ust.edu.ng https://orcid.org/0009-0005-2593-7873 References [1]. Le, V.; Kim Lien, V. T.; Pham, V. T.; Tran, Q. T.; Thuy, P. T.; Ha, C. V.; Doanh, V. V.; Ha, L. T.; Hanh, C. H.; Thao, P. N.; Luc, N. Effect of extended π-conjugation on photophysical characteristics of chalcone and cinnamylideneacetophenone. Mater. Sci. Semicond. Process. 2023, 162, 107507. [2]. Viswanathan, T.; Gopalakrishnan, M.; Thirumoorthy, K.; Prakash, M.; Palanisami, N. Enhancement of Second-Order Nonlinear Optical Properties of Centrosymmetric Ferrocenyl Borasiloxane by a Broken- Symmetry Approach. J. Phys. Chem. C. 2021, 125 (16), 8732–8740. [3]. Purushothaman, P.; Mohanapriya, D.; Thenmozhi, K.; Karpagam, S. Designing a ferrocene biphenyl pyridine modified electrode for the non-enzymatic electrochemical detection of catechol. New J. Chem. 2024, 48 (15), 6893–6901. [4]. Bull, O. S.; Don-Lawson, C.; Nweke-Maraizu, U. Synthesis and Characterization of a Novel Eight-Membered Cyclo-1,3,3,5,7,7- Hexaphenyl-1,5-Dibora-3,7-Disiloxane and 4,4ˈ-Bipyridine, 1D Adduct. Eur. J. Chem. 2024, 15 (3), 232–238. [5]. Bull, O. S.; Don-Lawson, C. Facile Heck coupling synthesis and characterization of a novel tris(4-(pyridine-4-vinyl)phenyl)methyl silane tridentate core. Eur. J. Chem. 2024, 15 (1), 71–73. [6]. Sergeant Bull, O.; Monsuru Adewale, S.; Okpa, E. Production of Biodiesel from Waste Cooking Oil using A Zinc-Based Metal-Organic Framework (Zn-MOF) As Catalyst. SSRG-IJAC 2024, 11 (1), 1–6. [7]. Bull, O.; Bull, I.; Amadi, G. Global Warming and Technologies for Carbon Capture and Storage. jasem 2020, 24 (9), 1671–1686. [8]. Bull, O.; Bull, I.; Amadi, G.; Odu, C. Covalent Organic Frameworks (COFS): A Review. J. Appl. Environ. Manag. 2022, 26 (1), 145–179. [9]. Bull, O. S.; George, D. M. C. Assessment of Fuel Properties of Biodiesel Obtained From African Pear (Dacryodeseludis) Seeds Oil. Int. J. Adv. Res. Sci. Eng. Technol. 2015, 2 (10), 894–898. [10]. Hiscock, L.; Maly, Kenneth E.; Dawe, Louise N., Synthesis, Properties, and Solid-State Structures of a Series of 6,13-Dicyanoheteropentacene Analogues: Towards New Liquid Crystalline Materials Theses and Dissertations (Comprehensive). (2018) 2073. https://scholars.wlu.ca/etd/2073 (accessed Jan 7, 2024). [11]. Gopalakrishnan, M.; Thirumoorthy, K.; Bhuvanesh, N. S.; Palanisami, N. Eight membered cyclic-borasiloxanes: synthesis, structural, photophysical, steric strain and DFT calculations. RSC. Adv. 2016, 6 (61), 55698–55709. [12]. Sheepwash, E.; Zhou, K.; Scopelliti, R.; Severin, K. Self-Assembly of Arylboronate Esters with Pyridyl Side Chains. Eur J. Inorg Chem 2013, 2013 (14), 2558–2563. [13]. Beckett, M. A.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K.; Owen, P.; Varma, K. cyclo-Boratrisiloxane and cyclo-diboratetrasiloxane derivatives and their reactions with amines: crystal and molecular structure of (p-BrC6H4BO)2(Ph2SiO)2. J. Organomet. Chem. 2000, 595 (2), 241–247. [14]. Bull, O. S.; Okpa, E. Application of Green Chemistry for the One-pot Preparation of Tris (4-bromophenyl) Chlorosilane. SSRG-IJAC 2023, 10 (2), 1–5. [15]. Bull, O. S. Silicon-Containing COFs and MOFs for CO2 Capture. Imperial College London 2018. https://doi.org/10.25560/83674 (accessed Jan 7, 2024). [16]. Gontarczyk, K.; Durka, K.; Klimkowski, P.; Luliński, S.; Serwatowski, J.; Woźniak, K. Synthesis and characterization of di-, tri- and tetraboronic acids based on phenyl- and thienylsilane cores. J. Organomet. Chem. 2015, 783, 1–9. [17]. Brisdon, B. J.; Mahon, M. F.; Molloy, K. C.; Schofield, P. J. Synthesis and structural characterization of cycloborasiloxanes: The X-ray crystal structures of cyclo-1,3,3,5,5-pentaphenyl-1-bora-3,5-disiloxane and cyclo-1,3,3,5,7,7-hexaphenyl-1,5-dibora-3,7-disiloxane. J. Organomet. Chem. 1992, 436 (1), 11–22. [18]. Foucher, D. A.; Lough, A. J.; Manners, I. Synthesis, properties, and the ring-ring transformation reactions of cyclic siloxanes incorporating skeletal boron atoms: x-ray crystal structures of the strained boracyclotrisiloxane (PhBO)(Ph2SiO)2 and the boracyclo tetrasiloxane (PhBO)(Ph2SiO)3. Inorg. Chem. 1992, 31 (14), 3034– 3043. [19]. Ferguson, G.; Lawrence, S. E.; Neville, L. A.; O’Leary, B. J.; Spalding, T. R. Synthetic and X-ray diffraction studies of borosiloxane cages [R′Si(ORBO)3SiR′] and the adducts of [ButSi{O(PhB)O}3SiBut] with pyridine or N,N,N′,N′-tetramethylethylenediamine. Polyhedron 2007, 26 (12), 2482–2492. [20]. O'Dowd, A. T.; Spalding, T. R.; Ferguson, G.; Gallagher, J. F.; Reed, D. Synthesis and crystal structure of the novel borosilicate cage compound [B(OSiPh2OSiPh2O)3B]. J. Chem. Soc., Chem. Commun. 1993, 1816–1817. [21]. Baykov, S. V.; Mikherdov, A. S.; Novikov, A. S.; Geyl, K. K.; Tarasenko, M. V.; Gureev, M. A.; Boyarskiy, V. P. π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study. Molecules 2021, 26 (18), 5672–5686. [22]. Tskhovrebov, A. G.; Novikov, A. S.; Odintsova, O. V.; Mikhaylov, V. N.; Sorokoumov, V. N.; Serebryanskaya, T. V.; Starova, G. L. Supramolecular polymers derived from the PtII and PdII schiff base complexes via C(sp2)–H…Hal hydrogen bonding: Combined experimental and theoretical study. J. Organomet. Chem. 2019, 886, 71–75. [23]. Nenajdenko, V. G.; Shikhaliyev, N. G.; Maharramov, A. M.; Bagirova, K. N.; Suleymanova, G. T.; Novikov, A. S.; Khrustalev, V. N.; Tskhovrebov, A. G. Halogenated Diazabutadiene Dyes: Synthesis, Structures, Supramolecular Features, and Theoretical Studies. Molecules 2020, 25 (21), 5013–5027. http://www.ccdc.cam.ac.uk/%20data_request/cif http://www.ccdc.cam.ac.uk/%20data_request/cif mailto:data_request@ccdc.cam.ac.uk mailto:bull.okpara@ust.edu.ng https://orcid.org/0000-0002-5810-1483 mailto:chioma.don-lawson@ust.edu.ng https://orcid.org/0009-0005-2593-7873 https://scholars.wlu.ca/etd/2073 https://doi.org/10.25560/83674 Bull and Don-Lawson / European Journal of Chemistry 15 (4) (2024) 325-331 331 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.4.325-331.2597 [24]. Ferguson, G.; Lough, A. J.; Sheehan, J. P.; Spalding, T. R. Structure of 2- (diphenylmethylsiloxy)-2-phenyl-1,3,2-oxazaborinane. Acta Crystallogr C. Cryst Struct Commun 1991, 47 (2), 379–381. [25]. Foucher, D. A.; Lough, A. J.; Manners, I. Synthesis, Properties, and the Ring-Ring Transformation Reactions of Cyclic Siloxanes Incorporating Skeletal Boron Atoms: X-Ray Crystal Structures of the Strained Boracyclotrisiloxane (PhBO)(Ph2SiO)2 and the Boracyclotetra siloxane (PhBO)(Ph2SiO)3. Inorg. Chem. 1992, 31 (14), 3034–3043. [26]. Arunan, E.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.; Crabtree, R. H.; Dannenberg, J. J.; Hobza, P.; Kjaergaard, H. G.; Legon, A. C.; Mennucci, B.; Nesbitt, D. J. Definition of the hydrogen bond (IUPAC Recommendations 2011). Pure Appl. Chem. 2011, 83 (8), 1637–1641. [27]. Sarveswari, S.; Srikanth, A.; Arul Murugan, N.; Vijayakumar, V.; Jasinski, J. P.; Beauchesne, H. C.; Jarvis, E. E. Synthesis, characterization of (3E)-1-(6-chloro-2-methyl-4-phenyl quinolin-3-Yl)-3-aryl prop-2- en-1-ones through IR, NMR, single crystal X-ray diffraction and insights into their electronic structure using DFT calculations. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 2015, 136, 1010–1017. Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry). https://www.eurjchem.com/index.php/eurjchem/terms http://creativecommons.org/licenses/by-nc/4.0 https://www.eurjchem.com/index.php/eurjchem/terms 1. Introduction 2. Experimental 2.1. Chemicals and reagents 2.2. Instrumentation 2.3. Synthesis 2.3.1. Synthesis of Ph6B2Si2O4 2.3.2. Synthesis of [Ph6B2Si2O4] L1 3. Results and discussion 4. Conclusions Acknowledgements Supporting information Disclosure statement CRediT authorship contribution statement ORCID and Email References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField15: PrintField16: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: PrintField25: PrintField26: