Citation: Wen-Xu ZHENG, Tao LI, Zheng XIANG, Chang-Cang HUANG. Cytosinium Isophthalate: Crystal Structure Redetermination and Room Temperature Phosphorescence[J]. Chinese Journal of Structural Chemistry, ;2020, 39(9): 1707-1713. doi: 10.14102/j.cnki.0254-5861.2011-2647 shu

Cytosinium Isophthalate: Crystal Structure Redetermination and Room Temperature Phosphorescence

College of Chemistry, Fuzhou University, Fuzhou 350108, China

Corresponding author: Chang-Cang HUANG, cchuang@fzu.edu.cn
Received Date: 24 October 2019
Accepted Date: 19 January 2020

Fund Project: the Natural Science Foundation of Fujian Province 2018J01688

Figures(8)

The title compound cytosinium isophthalate (C-H₂IA) self-assembly of cytosine (C) and isophthalic acid (H₂IA) in aqueous media has been synthesized and the crystal structure with a reasonable protonation state is redetermined. Single-crystal X-ray diffraction analysis reveals that each asymmetric unit contains one protoned cytosine molecule and one deprotoned isophthalic acid. The proton transferred from carboxylic acid to the pyrimidine ring is disordered across an inversion center with occupancy of 0.5 and the proton located to one of the carboxylate group lies on an inversion center shared by two crystallographically equivalent oxygen atoms. In addition, the cytosine molecules are connected by complementary hydrogen bonds to form a one-dimensional tape structure. The neighboring isophthalic acids are connected via hydrogen bonds between carboxyl groups to form a one-dimensional lattice like tape. Furthermore, the adjacent organic base tapes and organic acid tapes are stacked one with another through π-π stacking interactions to form a three-dimensional supramolecular structure. Interestingly, C-H₂IA displays a green phosphorescence in solid state at room temperature with the lifetime of 0.7 s determined by time resolved studies, indicating that supramolecular C-H₂IA is a potential pure organic phosphorescent luminogens.
- cytosinium isophthalate,
- crystal structure redetermination,
- room temperature phosphorescence,
- supramolecular framework
1. [1]
  Yang, Z.; Mao, Z.; Zhang, X. Intermolecular electronic coupling of organic units for efficient persistent room-temperature phosphorescence. Angew. Chem., Int. Ed. Engl. 2016, 55, 2181–2185. doi: 10.1002/anie.201509224
2. [2]
  (a) Kuei, C. Y.; Liu, S. H.; Chou, P. T. Room temperature blue phosphorescence: a combined experimental and theoretical study on the bis-tridentate Ir(Ⅲ) metal complexes. Dalton Trans. 2016, 45, 15364–15373; (b) Hirata, S. Recent advances in materials with room-temperature phosphorescence: photophysics for triplet exciton stabilization. Adv. Optical Mater. 2017, 5, 1700116–1700165.
3. [3]
  (a) Gong, Y.; Chen, G.; Peng, Q. Achieving persistent room temperature phosphorescence and remarkable mechanochromism from pure organic luminogens. Adv. Mater. 2015, 27, 6195–6201; (b) Xiao, L.; Wu, Y.; Chen, J. Highly efficient room-temperature phosphorescence from halogen-bonding-assisted doped organic crystals. J. Phys. Chem. A 2017, 121, 8652–8658.
4. [4]
  (a) Ge, C. H.; Zhang, X. Y.; Yu, F. Hydrogen-bonded assembly of Ni(Ⅱ) and Cu(Ⅱ) complexes generate 3D supramolecular frameworks. J. Chem. Crystallogr. 2008, 38, 501–505; (b) Nirmalram, J. S.; Tamilselvi, D.; Muthiah, P. T. Hydrogen bonded supramolecular assembly in N₆-benzyladeninium nitrate and N₆-benzyladeninium 3-hydroxy picolinate: a synthetic cytokinin. J. Chem. Crystallogr. 2011, 41, 864–867.
5. [5]
  Chen, J. The complexation between 'texas sized' molecular box and linear n-aliphate dianion: en route to supramolecular organic frameworks (SOFs) for selectively CO₂ absorption. Tetrahedron 2016, 72, 431–435. doi: 10.1016/j.tet.2015.11.062
6. [6]
  Ni, X. L.; Chen, S.; Yang, Y. Facile cucurbit[8]uril-based supramolecular approach to fabricate tunable luminescent materials in aqueous solution. J. Am. Chem. Soc. 2016, 138, 6177–6183. doi: 10.1021/jacs.6b01223
7. [7]
  Han, Z. B.; Xiao, Z. Z.; Hao, M. Functional hydrogen-bonded supramolecular framework for K⁺ ion sensing. Cryst. Growth Des. 2015, 15, 531–533. doi: 10.1021/cg501259g
8. [8]
  Lin, X. M.; Niu, J. L.; Wen, P. X. A polyhedral metal-organic framework based on supramolecular building blocks: catalysis and luminescent sensing of solvent molecules. Cryst. Growth Des. 2016, 16, 4705–4710. doi: 10.1021/acs.cgd.6b00779
9. [9]
  Zhang, Y.; Zhan, T. G.; Zhou, T. Y. Fluorescence enhancement through the formation of a single-layer two-dimensional supramolecular organic framework and its application in highly selective recognition of picric acid. Chem. Comm. 2016, 52, 7588–7591. doi: 10.1039/C6CC03631G
10. [10]
  Bian, L.; Shi, H.; Wang, X. Simultaneously enhancing efficiency and lifetime of ultralong organic phosphorescence materials by molecular self-assembly. J. Am. Chem. Soc. 2018, 140, 10734–10739. doi: 10.1021/jacs.8b03867
11. [11]
  Ebenezer, S.; Muthiah, P. T. Design of co-crystals/salts of aminopyrimidines and carboxylic acids through recurrently occurring xynthons. Cryst. Growth Des. 2012, 12, 3766–3785. doi: 10.1021/cg3005954
12. [12]
  Ayed, M.; Ayed, B.; Haddad, A. Synthesis and structural characterization of new inorganic-organic hybrid: arsenomolybdate compound with cytosinium cations. Bull. Mater. Sci. 2015, 38, 13–21. doi: 10.1007/s12034-014-0805-8
13. [13]
  Marsh, R. E.; Bierstedt, R.; Eichhorn, E. L. The crystal structure of cytosine-5-acetic acid. Acta Crystallogr. 1962, 15, 310–316. doi: 10.1107/S0365110X62000791
14. [14]
  Perumalla, S. R.; Suresh, E.; Pedireddi, V. R. Nucleobases in molecular recognition: molecular adducts of adenine and cytosine with COOH functional groups. Angew. Chem., Int. Ed. Engl. 2005, 44, 7752–7757. doi: 10.1002/anie.200502434
15. [15]
  Macrae, C. F.; Bruno, I. J.; Chisholm, J. A. Mercury CSD 2.0 - new features for the visualization and investigation of crystal structures. Journal of Applied Crystallogr. 2008, 41, 466–470. doi: 10.1107/S0021889807067908
16. [16]
  (a) Turner, M. J.; McKinnon, M. J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer17 (2017). University of Western Australia. http://hirshfeldsurface.net 2017; (b) Mackenzie, C. F.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer model energies and energy frameworks: extension to metal coordination compounds, organic salts, solvates and open-shell systems. IUCrJ 2017, 4, 575–587; (c) Bakavoli, M.; Rahimizadeh, M.; Feizyzadeh, B. 3,6-di(p-chlorophenyl)-2,7-dihydro-1,4,5-thiadiazepine: crystal structure and decoding intermolecular interactions with hirshfeld surface analysis. J. Chem. Crystallogr. 2010, 40, 746–752.
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