Structural and photoluminescent studies of non-centrosymmetric manganese(II) N-(2-pyridylmethyl)-(L)-alanine) dicyanamide European Journal of Chemistry 10 (3) (2019) 267-272 European Journal of Chemistry View Journal Online View Article Online Structural and photoluminescent studies of non-centrosymmetric manganese(II) N-(2-pyridylmethyl)-(L)-alanine) dicyanamide Bridget Ndoye Ndosiri 1,*, Katia Nchimi Nono 1, Paboudam Gbambie Awawou 1, Emmanuel Ngwang Nfor 2, Aminou Mohamadou 3, Jérôme Marrot 4 and Peter Ndifon Teke 1 1 Inorganic Chemistry Department, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon ndosirin@yahoo.com (B.N.N.), katia.nchimi@yahoo.fr (K.N.N.), unilawa@yahoo.fr (P.G.A), pndifon@yahoo.com (P.N.T) 2 Department of Chemistry, Faculty of Science, University of Buea, Buea, Cameroon nfor.emmanuel@ubuea.cm (E.N.N.) 3 Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims (ICMR), CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, Bâtiment 18 Europol ’Agro, BP 1039, F-51687 Reims Cedex 2, France aminou.mohamadou@univ-reims.fr (A.M.) 4 Institut Lavoisier de Versailles (ILV)-UMR 8180 (CNRS/UVSQ,)45 avenue des États-Unis Bâtiment Lavoisier 78035 Versailles, Cedex, France jerome.marrot@uvsq.fr (J.M.) * Corresponding author at: Inorganic Chemistry Department, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon. Tel: +237.67.7342996 Fax: +237.22.2233965 e-mail: ndosirin@yahoo.com (B.N. Ndosiri). 10.5155/eurjchem.10.3.267-272.1914 Received: 05 July 2019 Received in revised form: 29 July 2019 Accepted: 31 July 2019 Published online: 30 September 2019 Printed: 30 September 2019 The dinuclear compound, [Mn2(Pyala)2(Dca)2(H2O)]n·2H2O (1) (Pyala = N-(2- pyridylmethyl)-L-alanine and Dca = dicyanamide anion) has been synthesized and characterized by elemental analysis, IR and single crystal X-ray diffraction techniques. The crystal data for C22H26Mn2N10O6: orthorhombic, space group P212121 (no. 19), a = 10.3728(8) Å, b = 15.9780(12) Å, c = 16.3585(13) Å, V = 2711.2(4) Å3, Z = 4, T = 198(2) K, μ(MoKα) = 0.989 mm-1, Dcalc = 1.559 g/cm3, 129607 reflections measured (3.564° ≤ 2Θ ≤ 60.046°), 7923 unique (R int = 0.0324, Rsigma = 0.0155) which were used in all calculations. The final R1 was 0.0169 (I > 2σ(I)) and wR2 was 0.0458 (all data). The obtained non- centrosymmetric dinuclear Mn(II) complex contains two unique Mn(II) cations with similar octahedral coordination environment. Photoluminescent measurements on the complex in the solid state show that it displays strong photoluminescence at 442 nm. Manganese Dicyanamide Photoluminescent Non-centrosymmetric Single crystal structure N-(2-Pyridylmethyl)-(L)-alanine) Cite this: Eur. J. Chem. 2019, 10(3), 267-272 Journal website: www.eurjchem.com 1. Introduction The recent development in designing the novel solid-state structures and preparation of polynuclear complexes with one-, two- or three-dimensional homo- or hetero-thallic infinite frameworks and also mono- and di-nuclear complexes are the subject of great interest due to their widespread applications in various fields like molecular magnetism, photochemical activity, intervalence electron transfer reaction and catalytic reactions [1-3]. The pseudo halide ligand dicyanamide (Dca, [N(CN)2]-), which was first utilized by Köhler [4-7], has been widely studied for many years to design polymeric structures [8]. It is a remarkably versatile building block for the construction of metal-organic architectures, since it can act as a mono-, bi- and tri-dentate ligand, yielding a variety of novel structures [9]. A notable feature of metal-Dca coordination polymers is the ability of cations to template anionic [M(Dca)3]- networks [10]. The prime cases of previously reported three-dimensional metal-Dca networks are neutral binary systems. The series MX2 (X: [N(CN)2]-; M: Cr2+, Mn2+, Co2+, Ni2+ or Cu2+) and related complexes have attracted increased interest because of their rutile-like structures containing chains of doubly-bridged metal atoms with M(NCNCN)M units [11]. The pseudo halide, dca ligand has been seen in many cases to play an instructive role in building coordination polymers. On the other hand, non-centrosymmetric materials are of particular importance in the field of material chemistry for the large number of symmetry-dependent properties, they can possess, including circular dichroism, pyroelectricity, and non- linear optical behavior [12-14]. While purposefully enginee- ring these materials can be difficult, one method for elimina- ting centrosymmetry in crystalline materials is co-crystal- lization with an enantiopure chiral compound [15]. In this ABSTRACT RESEARCH ARTICLE KEYWORDS European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2019 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. http://dx.doi.org/10.5155/eurjchem.10.3.267-272.1914 http://dx.doi.org/10.5155/eurjchem.10.3.267-272.1914 https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.10.3.267-272.1914&domain=pdf&date_stamp=2019-09-30 http://www.eurjchem.com/ http://dx.doi.org/10.5155/eurjchem.10.3.267-272.1914 mailto:ndosirin@yahoo.com mailto:katia.nchimi@yahoo.fr mailto:unilawa@yahoo.fr mailto:pndifon@yahoo.com mailto:nfor.emmanuel@ubuea.cm mailto:aminou.mohamadou@univ-reims.fr mailto:jerome.marrot@uvsq.fr mailto:ndosirin@yahoo.com http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.10.3.267-272.1914&domain=pdf&date_stamp=2019-09-30� 268 Ndosiri et al. / European Journal of Chemistry 10 (3) (2019) 267-272 Table 1. Crystal data and details of the structure refinement for compound 1. Parameters Compound 1 Empirical formula C 22H26Mn2N10O6 Formula weight 636.41 Temperature (K) 198(2) Crystal system Orthorhombic Space group P212121 a (Å) 10.3728(8) b (Å) 15.9780(12) c (Å) 16.3585(13) Volume (Å3) 2711.2(4) Z 4 ρ calc (g/cm3) 1.559 μ(mm-1) 0.989 F(000) 1304.0 Crystal size (mm3) 0.280 × 0.220 × 0.100 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 3.564 to 60.046 Index ranges -12 ≤ h ≤ 14, -22 ≤ k ≤ 22, -22 ≤ l ≤ 22 Reflections collected 129607 Independent reflections 7923 [Rint = 0.0324, Rsigma = 0.0155] Data/restraints/parameters 7923/5/400 Goodness-of-fit on F2 1.035 Final R indexes [I≥2σ (I)] R1 = 0.0169, wR2 = 0.0455 Final R indexes [all data] R1 = 0.0178, wR2 = 0.0458 Largest diff. peak/hole (e.Å-3) 0.22/-0.18 Flack parameter 0.008(2) N H N OH O CH3H N O H3C OH O NH2 MeOH/KOH NaBH4 / H2O H Scheme 1. Synthetic scheme of N-(2-pyridylmethyl)-L-alanine. way, provided that the chiral compound is not capable of racemization, the potential point groups are limited only to those which are chiral, and therefore non-centrosymmetric. The amino acid L-alanine plays an important role in deter- mining the structure of proteins, due to its structural rigidity. L-alanine has also been shown to be a good candidate for synthesizing non-centrosymmetric co-crystals [16]. Inspired by these considerations, and in continuation with studies on Pyala ligand [17], we elected to study the reaction between manganese (II) and dicyanamide anion in the presence of chiral bridging ligand, N-(2-pyridylmethyl)-L-alanine. 2. Experimental 2.1. Materials and physical measurements All reagents and solvents used for the synthesis were of reagent grade. Manganese acetate tetrahydrate and sodium dicyanamide were from commercial sources and used without further purification. Ethanol was dried and distilled according to standard methods. Elemental analysis for carbon, nitrogen and hydrogen were carried out on a Fisons instrument 1108 CHNS-O. Luminescence spectra were measured on a HitachiF- 4500 spectrophotometer at room temperature. The X-ray diffraction was carried out with a CCD bidimensional diffracto- meter using monochromatic radiation, λ(MoKα) = 0.71073 Å, operating at 50 kV and 40 mA. The crystal structure of [Mn2(Pyala)2(Dca)2(H2O)]n·H2O (1) was determined by single crystal X-ray diffraction on a Bruker APEX-II using monochro-matic MoKα radiation (λ = 0.71073 Å) at a temperature of 198 K and integrated with SAINT-Plus program [18], and absorption corrections were carried out by multi-scan method by SADABS [19]. The structure was solved by direct methods and refined against F2 by full-matrix least- squares techniques with SHELXTL [20]. All non-hydrogen atoms were refined with anisotropic displacement parameters. Hydrogen atoms were included from calculated positions and refined riding their respective parent atoms with isotropic displacement parameters. 2.2. Synthesis of [Mn2 (Pyala)2(Dca)2(H2O)]n·2H2O (1) Synthesis of N-(2-pyridylmethyl)-L-alanine (Pyala) was as reported in literature (Scheme 1) [16]. Pyala (0.36 g, 2 mmol,) in 10 mL water:ethanol mixture (1:1, v:v) was added drop wise to a 5 mL aqueous solution of Mn(OOCH3)2·4H2O (0.245 g, 1 mmol), while stirring magnetically at room temperature. After stirring for a further 10 minutes, NaN(CN)2 (0.18 g, 2 mmol) in 5 mL distilled water was added drop wise and stirring continued for two hours. Suitable parallelepiped colorless crystals for X-ray analysis were obtained from the solution by slow evaporation. Yield: 70%. Anal. calcd. for C11H13MnN5O3; C, 41.52; H, 4.12; N, 22.01. Found: C, 41.46; H, 4.07; N, 22.59%. 3. Results and discussion The crystal structure refinement data for compound 1 is presented in Table 1. The selected bond lengths and angles are given in Table 2. The structure of [Mn2(Pyala)2(Dca)2 (H2O)]·2H2O and its atom numbering scheme is shown in Figure 1. As shown in Figure 1, there are two unique octahed- rally coordinated Mn2+ cations (Mn1 and Mn2) with similar coordination modes. Each Mn2+ is coordinated to one Pyala ligand via N1, N8 and N24, N17; and bridged by the two carboxylate oxygen atoms (O3, O4 and O1, O2). The octahedral geometry around Mn1 is completed by one water molecule oxygen (O5W) and one Dca nitrogen (N12), while the octahedral geometry around Mn2 is completed by the coordination of two Dca nitrogen atoms, (N28 and N16) in a monodentate manner. Each Mn2+ center is connected by end- to-end μ-1,5-Dca bridge via N12 and N16 in successive chains to form a 1D structure (Figure 2). 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.267-272.1914 Ndosiri et al. / European Journal of Chemistry 10 (3) (2019) 267-272 269 Table 2. Selected bond lengths [Å] and bond angles [°] for compound 1*. Bond lengths Mn1-O3 2.1383(10) Mn2-O2 2.1386(10) Mn1-O5 2.1633(12) Mn2-O4i 2.1928(10) Mn1-O1 2.1844(10) Mn2-N16ii 2.2087(12) Mn1-N12 2.2069(13) Mn2-N28 2.2246(12) Mn1-N8 2.3262(11) Mn2-N17i 2.2662(11) Mn1-N1 2.3280(12) Mn2-N24i 2.3355(11) Bond angles O3-Mn1-O5 90.02(5) O2-Mn2-O4i 176.77(4) O3-Mn1-O1 175.11(4) O2-Mn2-N16ii 90.56(5) O5-Mn1-O1 86.36(4) O4i-Mn2-N16ii 92.08(4) O3-Mn1-N12 93.33(5) O2-Mn2-N28 94.02(5) O5-Mn1-N12 95.50(5) O4i-Mn2-N28 87.82(4) O1-Mn1-N12 90.30(5) N16ii-Mn2-N28 90.36(5) O3-Mn1-N8 107.86(4) O2-Mn2-N17i 88.71(4) O5-Mn1-N8 157.12(5) O4i-Mn2-N17i 88.56(4) O1-Mn1-N8 74.87(4) N16ii-Mn2-N17i 177.15(5) N12-Mn1-N8 97.52(5) N28-Mn2-N17i 92.43(4) O3-Mn1-N1 89.80(4) O2-Mn2-N24i 103.37(4) O5-Mn1-N1 91.97(5) O4i-Mn2-N24i 74.26(4) O1-Mn1-N1 87.04(4) N16ii-Mn2-N24i 101.99(4) N12-Mn1-N1 171.89(5) N28-Mn2-N24i 158.42(4) N8-Mn1-N1 74.40(4) N17i-Mn2-N24i 75.51(4) * Symmetry transformations used to generate equivalent atoms: (i) x+1, y, z; (ii) -x+2, y+1/2, -z+3/2. (a) (b) Figure 1. Molecular structure (a) and the coordination environment of the Mn1 and Mn2 atoms (b) in compound 1 showing the atom numbering scheme. In addition, this coordination polymer consists of Mn2N4O2 and Mn1N3O3 octahedral units as illustrated in Figure 3. The Mn-O bond distances in compound 1 are in the range of 2.1382(5)-2.1926(4) Å, with the Mn-Owater bond length (2.1643(5) Å) longer than the Mn-Ocarboxylate bond length (2.1382(5) Å). Furthermore, all the Mn-Ndca bond distances are in the range of 2.2069(6)-2.2255(6) Å and are in good agree-ments with previously published results [21-23]. These Mn-Ndca bond distances are all shorter than the Mn-Npyridyl bond distances of 2.3326(5)-2.3362(4) Å, also consistent with earlier reports of a similar compound [16,24]. These are clear indications that the Mn-Ndca bonds are stronger than the Mn- Npyridyl bonds. Overall the Mn-O bond distances are shorter than the Mn-N bond distances in compound 1. 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.267-272.1914 270 Ndosiri et al. / European Journal of Chemistry 10 (3) (2019) 267-272 Figure 2. Schematic view of the “S” type double stranded helical chains of compound 1. Figure 3. The octahedral chaining of MnN4O2 and MnN3O3. Figure 4. Packing along the a axis showing chiral channels. The basal plane of the octahedron around the Mn1 center (O1, O3 and N12, N1) are almost trans to each other, with respective bond angles O1-Mn1-O3 (175.102(4)° and N12- Mn1-N1 (171.90(4)°). Similarly, the basal plane of the octahedron around Mn2 center (O2, O4 and N16, N17) are also almost trans to each other, with respective bond angles of O2- Mn2-O4 (176.78(4)° and N16-Mn2-N17(177.10(4)°). The shortest Mn-Mn separation through the pyala-bridge is 5.458(4) Å. while the distance between successive Mn1-Mn1 or Mn2-Mn2 atoms along the polymeric chain is 10.373(8) Å which is similar to previously reported results of manganese dicyanamide complex [25]. The neighbouring Mn2+ cation are linked together by double dca bridges to form a one- dimensional polymeric chain connected to each other through hydrogen bonding. Compound 1 was found to exhibit some chiral channels as depicted in Figure 4. Intramolecular hydrogen bondings as well, exist in compound 1 and thus help in reinforcing the supramolecular structure. 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.267-272.1914 Ndosiri et al. / European Journal of Chemistry 10 (3) (2019) 267-272 271 Figure 5. Photoluminescence spectra of compound 1. 3.1. Photoluminescent behaviour of compound 1 The photoluminescent (PL) properties of the compound were examined in solid state at room temperature (Figure 5). This compound exhibited strong fluorescent emission at 377 and 442 nm, upon excitation at 341 and 385 nm, respectively. In other to understand the nature of the emission, we examined the photoluminescence property of the free ligand and found that, the strongest emission peak is at 391 and 432 nm (λex = 368 nm). Therefore, the luminescence of the compound 1 may be attributed to metal to ligand charge transfer (MLCT) or ligand to metal charge (LMCT) [26-28]. These observations suggest that compound 1 may be a good candidate for potential photoactive materials. 4. Conclusion A new non-centrosymmetric manganese (II) coordination polymer of N-(2-pyridylmethyl)-(L)-alanine and dicyanamide anion in both terminal unidentate and end-to-end μ-1,5- bonding modes has been obtained. The dinuclear compound has two unique Mn2+ centers. Each Mn2+ center is connected by end-to-end μ-1,5-dca bridge in successive chains to form a 1-D structure. The octahedron around the manganese (II) centers consists of Mn2N4O2 and Mn1N3O3 moieties. The stability of the complex is enhanced by N···H and O···H hydrogen bonding interactions. A photoluminescent measurement on the complex in the solid state shows that it displays strong photo- luminescence at 442 nm. Acknowledgements The authors gratefully acknowledge Dr. Namanga Jude Eko, Scientist at OSRAM for the photoluminescence analysis. Supporting information CCDC 1508113 contains the supplementary crystallo- graphic data for this paper. These data can be obtained free of charge viahttps://www.ccdc.cam.ac.uk/structures/, 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 interests: The authors declare that they have no conflict of interest. Author contributions: All authors contributed equally to this work. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compounds are available from the author. ORCID Bridget Ndoye Ndosiri http://orcid.org/0000-0001-7969-8963 Katia Nchimi Nono http://orcid.org/0000-0002-5031-6404 Paboudam Gbambie Awawou http://orcid.org/0000-0002-2194-0072 Emmanuel Ngwang Nfor http://orcid.org/0000-0003-4941-3917 Aminou Mohamadou http://orcid.org/0000-0002-6140-4186 Jérôme Marrot http://orcid.org/0000-0002-5351-4908 Peter Ndifon Teke http://orcid.org/0000-0001-9331-9034 References [1]. Sen, S. Beats Natur. Sci. 2016, 1(3), 1-6. [2]. Nfor, E. N.; Majoumo-Mbe, F.; Ndifon, P. T.; Duke, E. O.; Mainsah, E. N.; Offiong, O. E.; Eno, A. E. J. Solid State Chem. 2013, 201, 133-136. [3]. Ye, Q.; Shi, P. P.; Fu, X. Q.; Akutagawa, T.; Nakamura, T. Cryst. Eng. Comm. 2013, 15, 5307-5313. [4]. Jun, L.; Lijuan, Q.; Baoshu, L.; Xinrong, Z.; Feng, Y.; Lili, C. Chinese J. Chem. 2012, 30, 522-528. [5]. 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Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry). 2019 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.10.3.267-272.1914 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms http://creativecommons.org/licenses/by-nc/4.0 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms 1. Introduction 2. Experimental 2.1. Materials and physical measurements 2.2. Synthesis of [Mn2 (Pyala)2(Dca)2(H2O)]n 2H2O (1) 3. Results and discussion 3.1. Photoluminescent behaviour of compound 1 4. Conclusion Acknowledgements Supporting information Disclosure statement ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField15: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: PrintField25: