Citation: Zhao-Hua CHEN, Cai-Hua GUO, Zhen-Hua LU, Qin-Tian YANG. Hydrogen Bond-driven Assembly of Stilbazolium Dye with Zinc Chloride: X-aggregation Induced Photoluminescence and Dual Stimuliresponsive Performance[J]. Chinese Journal of Structural Chemistry, ;2020, 39(10): 1841-1848. doi: 10.14102/j.cnki.0254–5861.2011–2714 shu

Hydrogen Bond-driven Assembly of Stilbazolium Dye with Zinc Chloride: X-aggregation Induced Photoluminescence and Dual Stimuliresponsive Performance

College of Food and Biological Engineering, Jimei University, Xiamen, Fujian 361021, China

Corresponding author: Zhao-Hua CHEN, zhchen@jmu.edu.cn
Received Date: 23 December 2019
Accepted Date: 28 February 2020

Figures(7)

Combination of D-π-A stilbazolium-type dye DANP (DANP = trans-4-(4΄-(N, N-diethylaminostyryl))-N-methyl-pyridinium) with zinc chloride results in a new hybrid (DANP-H)(ZnCl₄) (1), and its structure was determined by single-crystal X-ray diffraction method. In the hybrid, two independent DANP-H²⁺ cations exhibit two kinds of configurations, i.e., conjugation-broken and conjugation-maintained fashions, and the X-aggregation mode of (DANP-H)²⁺ cations is driven by strong C–H···Cl hydrogen bonds and C–H···π interactions. Consequently, blue-shift was observed in its adsorption spectrum, and unquenched red photoluminescence can be monitored. Interestingly, dual stimuli-responsive performance and reversible photo/thermochromic behaviors appeared, which can be assigned to the electron transfer from Cl-3p/DANP-π to π* antibonding orbitals of the conjugation-maintained DANP.
- stilbazolium-type dye,
- zinc chloride,
- X-aggregation,
- photoluminescence,
- photo/thermochromism
1. [1]
  Cariati, E.; Lucenti, E.; Botta, C.; Giovanella, U.; Marinotto, D.; Righetto, S. Cu(I) hybrid inorga-organic materials with intriguing stimuli responsive and optoelectronic properties. Coord. Chem. Rev. 2016, 306, 566−614. doi: 10.1016/j.ccr.2015.03.004
2. [2]
  Wang, Y. K.; Zhao, L. M.; Fu, Y. Q.; Chen, Z.; Lin, X. Y.; Wang, D. H.; Li, Y.; Li, H. H.; Chen, Z. R. Combination of N-arylstilbazolium organic nonlinear optical chromophores with iodoargentates: structural diversities and optical properties. Cryst. Growth Des. 2018, 18, 3827−3840. doi: 10.1021/acs.cgd.8b00033
3. [3]
  Sun, Z. H.; Luo, J. H.; Chen, T. L.; Li, L. N.; Xiong, R. G.; Tong, M. L.; Hong, M. C. Distinct molecular motions in a switchable chromophore dielectric 4-N, N-dimethylamino-4΄-N΄-methylstilbazolium trifluoromethanesulfonate. Adv. Funct. Mater. 2012, 22, 4855−4861. doi: 10.1002/adfm.201201770
4. [4]
  Pan, F.; Wong, M. S.; Bosshard, C.; Gunter, P. Crystal growth and characterization of the organic salt 4-N, N-dimethylamino-4΄-N-methyl-stilbazolium tosylate (dast). Adv. Mater. 1996, 8, 592−595.
5. [5]
  Zhao, L. M.; Shen, X. Q.; Zhang, W. T.; Song, K. Y.; Li, H. H.; Chen, Z. R. Encapsulation of stilbazolium-type dyes into layered metal-organic frameworks: solvent-dependent luminescence chromisms and their mechanisms. Inorg. Chem. Front. 2019, 6, 1195–1208. doi: 10.1039/C8QI01332B
6. [6]
  Uda, K.; Tsuda, Y.; Okada, S.; Yamakado, R.; Sun, L.; Suzuri, Y.; White, M. S.; Furis, M.; Stadler, P.; Dimitriev, O.; Yoshida, T. Concerted photoluminescence of electrochemically self-assembled CuSCN/stilbazolium dye hybrid thin films. ACS Omega. 2019, 4, 4056−4062. doi: 10.1021/acsomega.8b03632
7. [7]
  Wolf, T.; Niazov-Elkan, A.; Sui, X. M.; Weissman, H.; Bronshtein, I.; Raphael, M.; Wagner, H. D.; Rybtchinski, B. Free-standing nanocrystalline materials assembled from small molecules. J. Am. Chem. Soc. 2018, 140, 4761−4764. doi: 10.1021/jacs.7b13638
8. [8]
  Karuppanan, N.; Kalainathan, S. A new nonlinear optical stilbazolium family crystal of (E)-1-ethyl-2-(4-nitrostyryl)pyridin-1-ium iodide: synthesis, crystal structure, and its third-order nonlinear optical properties. J. Phys. Chem. C 2018, 122, 4572−4582. doi: 10.1021/acs.jpcc.7b11884
9. [9]
  Yang, Z.; Mutter, L.; Stillhart, M.; Ruiz, B.; Aravazhi, S.; Jazbinsek, M.; Schneider, A.; Gramlich, V.; Günter, P. Large-size bulk and thin-film stilbazolium-salt single crystals for nonlinear optics and THz generation. Adv. Funct. Mater. 2007, 17, 2018−2023. doi: 10.1002/adfm.200601117
10. [10]
  Li, D.; Sun, X.; Shao, N.; Wu, J.; Tian, Y. Self-assembly of organic chromosphere cations with inorganic lanthanide(III) complex counterions. Z. Anorg. Allg. Chem. 2014, 640, 2283–2286. doi: 10.1002/zaac.201400116
11. [11]
  Wu, J.; Hua, G.; Wang, P.; Hao, F.; Zhou, H.; Zhou, A.; Tian, Y.; Jin, B. Organic/polyoxometalate hybridization dyes: crystal structure and enhanced two-photon absorption. Dyes Pigm. 2011, 88, 174–179. doi: 10.1016/j.dyepig.2010.06.004
12. [12]
  Li, D.; Zhang, Q.; Sun, X.; Shao, N.; Li, R.; Li, S.; Zhou, H.; Wu, J.; Tian, Y. Hydrosoluble two-photon absorbing materials: a series of sulfonated organic inner salts in biological imaging application. Dyes Pigm. 2014, 102, 79–87. doi: 10.1016/j.dyepig.2013.10.028
13. [13]
  Hestand, N. J.; Spano, F. C. Expanded theory of H- and J-molecular aggregates: the effects of vibronic coupling and intermolecular charge transfer. Chem. Rev. 2018, 118, 7069–7163. doi: 10.1021/acs.chemrev.7b00581
14. [14]
  Cariati, E.; Macchi, R.; Roberto, D.; Ugo, R.; Galli, S.; Casati, N.; Macchi, P.; Sironi, A.; Bogani, L.; Caneshi, A.; Gatteschi, D. Polyfunctional inorganic-organic hybrid materials: an unusual kind of NLO active layered mixed metal oxalates with tunable magnetic properties and very large second harmonic generation. J. Am. Chem. Soc. 2007, 129, 9410−9420. doi: 10.1021/ja0710712
15. [15]
  Lacroix, P. G.; Munoz, M. C.; Gaspar, A. B.; Real, J. A.; Bonhommeau, S.; Rodriguez, V.; Nakatani, K. Synthesis, crystal structures, and solid state quadratic nonlinear optical properties of a series of stilbazolium cations combined with gold cyanide counter-ion. J. Mater. Chem. 2011, 21, 15940−15949. doi: 10.1039/c1jm12105g
16. [16]
  Cariati, E.; Ugo, R.; Cariati, F.; Roberto, D.; Masciocchi, M.; Galli, S.; Sironi, A. J-aggregates granting giant second-order NLO responses in self-assembled hybrid inorganic-organic materials. Adv. Mater. 2001, 13, 1665−1668. doi: 10.1002/1521-4095(200111)13:22<1665::AID-ADMA1665>3.0.CO;2-X
17. [17]
  Compain, J. D.; Mialane, P.; Dolbecq, A.; Marrot, J.; Proust, A.; Nakatani, K.; Yu, P.; Secheresse, F. Second-order nonlinear optical properties of polyoxometalate Ssalts of a chiral stilbazolium derivative. Inorg. Chem. 2009, 48, 6222−6228. doi: 10.1021/ic900519p
18. [18]
  Wang, M.; Yang, C.; Wang, G. E.; Xu, G.; Lv, X. Y.; Xu, Z. N.; Lin, R. G.; Cai, L. Z.; Guo, G. C. A room-temperature X-ray-induced photochromic material for X-ray detection. Angew. Chem. Int. Ed. 2012, 124, 3488–3491. doi: 10.1002/ange.201108220
19. [19]
  Tian, Y.; Li, F.; Zhang, G. C.; Zhou, H. P.; Wu, J. Y.; Tian, Y. P. Two solid fluorescent organic-inorganic hybrids: synthesis, crystal structures and strong red fluorescence emissions. Chin. J. Inorg. Chem. 2017, 33, 664–672. (20) Lee, S. H.; Kang, B. J.; Yoo, B. W.; Lee, S. C.; Lee, S. J.; Jazbinsek, M.; Yun, H.; Rotermund, B.; Kwon, O. Terahertz phonon mode engineering of highly efficient organic terahertz generators. Adv. Funct. Mater. 2017, 27, 1605583(1–9).
20. [20]
  Perew, J. P.; Burke, K.; Ernzerhof, M. Generalized gradient approximation made simple. Phy. Rev. Lett. 1996, 77, 3865–3868. doi: 10.1103/PhysRevLett.77.3865
21. [21]
  Segall, M.; Probert, M.; Pickard, C.; Hasnip, P.; Clark, S.; Refson, K.; Payne, M. First principles methods using CASTEP. Z. Krystallogr. 2005, 220, 567–570.
22. [22]
  Sheldrick, G. M. SHELXS-97: Program for the Solution of Crystal Structures. University of Gottingen, Germany 1997.
23. [23]
  Sheldrick, G. M. SHELXL-97: Program for the Refinement of Crystal Structures. University of Gottingen, Germany 1997.
24. [24]
  Chen, W. T.; Hu, R. H.; Luo, Z. G.; Chen, H. L.; Zhang, X. N.; Liu, J. [N-ethyl-4, 4΄-bipyridinium][ZnX₄] (X = Cl or Br) with N-ethyl-4, 4΄-bipyridinium generated in situ: syntheses, structures, fluorescence and TDDFT calculations. Chin. J. Struct. Chem. 2014, 33, 1141–1146.
25. [25]
  Chen, C. H.; Xu, G. C. Synthesis, characterization and disorder-order phase transition of inorganic-organic hybrid materials (H₂dabco-CH₂-Cl)M^IICl₄] (M = Co, Zn). CrystEngComm. 2016, 18, 550–557. doi: 10.1039/C5CE02059J
26. [26]
  Marder, S. R.; Perry, J. W.; Bourhill, G.; Gorman, C. B.; Tiemann, B. G.; Mansour, K. Relationbetween bond-length alternation and second electronic hyperpolarizability of conjugated organic molecules. Science 1993, 261, 186–189. doi: 10.1126/science.261.5118.186
27. [27]
  Xie, Z.; Yang, B.; Li, F.; Cheng, G.; Liu, L.; Yang, G.; Xu, H.; Ye, L.; Hanif, M.; Liu, S.; Ma, D.; Ma, Y. Cross dipole stacking in the crystal of distyrylbenzene derivative: the approach toward high solid-state luminescence efficiency. J. Am. Chem. Soc. 2005, 127, 14152–14153. doi: 10.1021/ja054661d
28. [28]
  Cariati, E.; Macchi, R.; Roberto, D.; Ugo, R.; Galli, S.; Masciocchi, N.; Sironi, A. Sequential self-organization of silver(I) layered materials with strong SHG by J-aggregation and intercalation of organic nonlinear optical chromophores through mechanochemical synthesis. Chem. Mater. 2007, 19, 3704–3711. doi: 10.1021/cm071003e
29. [29]
  Xu, G.; Li, Y.; Zhou, W. W.; Wang, G. J.; Long, X. F.; Cai, L. Z.; Wang, M. S.; Guo, G. C.; Huang, J. S.; Batorb, G.; Jakubas, R. A ferroelectric inorganic-organic hybrid based on NLO-phore stilbazolium. J. Mater. Chem. 2009, 19, 2179–2183. doi: 10.1039/b819473d
30. [30]
  Kolev, T.; Koleva, B. B.; Seidel, R. W.; Spiteller, M.; Sheldrick, W. S. New aspects on the origin of color in the solid state. Coherently shifting of the protons in violurate crystals. Cryst. Growth Des. 2009, 9, 3348–3352. doi: 10.1021/cg900188k
31. [31]
  Cai, S.; Wang, M. S.; Li, P. X.; Guo, G. C. Conductance switch of a bromoplumbate bistable semiconductor by electron-transfer thermochromism. Angew. Chem. Int. Ed. 2017, 56, 554–558. doi: 10.1002/anie.201610180
32. [32]
  Lin, R. G.; Xu, G.; Wang, M. S.; Lu, G.; Li, P. X.; Guo, G. C. Improved photochromic properties on viologen-based inorganic-organic hybrids by using π-conjugated substituents as electron donors and stabilizers. Inorg. Chem. 2013, 52, 1199−1205. doi: 10.1021/ic301181b
33. [33]
  Xu, G.; Guo, G. C.; Wang, M. S.; Zhang, Z. J.; Chen, W. T.; Huang, J. S. Photochromism of a methyl viologen bismuth(III) chloride: structural variation before and after UV irradiation. Angew. Chem. Int. Ed. 2007, 46, 3249–3251. doi: 10.1002/anie.200700122
1. [1]
  Zheyu Li , Huwei Li , Yao Li , Xinyu Fu , Hongxia Yue , Qingxing Yang , Jing Feng , Xinyu Wang , Hongjie Zhang . The effect of electron-phonon coupling on the photoluminescence properties of zinc-based halides. Chinese Chemical Letters, 2025, 36(4): 109800-. doi: 10.1016/j.cclet.2024.109800
2. [2]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388
3. [3]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
4. [4]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
5. [5]
  Yanting HUANG , Hua XIANG , Mei PAN . Construction and application of multi-component systems based on luminous copper nanoclusters. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2075-2090. doi: 10.11862/CJIC.20240196
6. [6]
  Hang Meng , Bicheng Zhu , Ruolun Sun , Zixuan Liu , Shaowen Cao , Kan Zhang , Jiaguo Yu , Jingsan Xu . Dynamic photoluminescence switching of carbon nitride thin films for anticounterfeiting and encryption. Chinese Journal of Structural Chemistry, 2024, 43(10): 100410-100410. doi: 10.1016/j.cjsc.2024.100410
7. [7]
  Yiqiao Chen , Ao Liu , Biwen Yang , Zhenzhen Li , Binggang Ye , Zhouyi Guo , Zhiming Liu , Haolin Chen . Photoluminescence and photothermal conversion in boric acid derived carbon dots for targeted microbial theranostics. Chinese Chemical Letters, 2024, 35(9): 109295-. doi: 10.1016/j.cclet.2023.109295
8. [8]
  Tiantian Gong , Yanan Chen , Shuo Wang , Miao Wang , Junwei Zhao . Rigid-flexible-ligand-ornamented lanthanide-incorporated selenotungstates and photoluminescence properties. Chinese Journal of Structural Chemistry, 2024, 43(9): 100370-100370. doi: 10.1016/j.cjsc.2024.100370
9. [9]
  Huan Hu , Ying Zhang , Shi-Shuang Huang , Zhi-Gang Li , Yungui Liu , Rui Feng , Wei Li . Temperature- and pressure-responsive photoluminescence in a 1D hybrid lead halide. Chinese Journal of Structural Chemistry, 2024, 43(10): 100395-100395. doi: 10.1016/j.cjsc.2024.100395
10. [10]
  Peipei CUI , Xin LI , Yilin CHEN , Zhilin CHENG , Feiyan GAO , Xu GUO , Wenning YAN , Yuchen DENG . Transition metal coordination polymers with flexible dicarboxylate ligand: Synthesis, characterization, and photoluminescence property. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2221-2231. doi: 10.11862/CJIC.20240234
11. [11]
  Xiao-Tong Sun , Hao-Fei Ni , Yi Zhang , Da-Wei Fu . Hybrid perovskite shows temperature-dependent photoluminescence and dielectric response triggered by halogen substitution. Chinese Journal of Structural Chemistry, 2024, 43(6): 100212-100212. doi: 10.1016/j.cjsc.2023.100212
12. [12]
  Xuan Zhu , Lin Zhou , Xiao-Yun Huang , Yan-Ling Luo , Xin Deng , Xin Yan , Yan-Juan Wang , Yan Qin , Yuan-Yuan Tang . (Benzimidazolium)2GeI4: A layered two-dimensional perovskite with dielectric switching and broadband near-infrared photoluminescence. Chinese Journal of Structural Chemistry, 2024, 43(6): 100272-100272. doi: 10.1016/j.cjsc.2024.100272
13. [13]
  Kailong Zhang , Chao Zhang , Luanhui Wu , Qidong Yang , Jiadong Zhang , Guang Hu , Liang Song , Gaoran Li , Wenlong Cai . Chloride molten salt derived attapulgite with ground-breaking electrochemical performance. Chinese Chemical Letters, 2024, 35(10): 109618-. doi: 10.1016/j.cclet.2024.109618
14. [14]
  Yu He , Hao Jiang , Shaoxuan Yuan , Jiayi Lu , Qiang Sun . On-surface photo-induced dechlorination. Chinese Chemical Letters, 2024, 35(9): 109807-. doi: 10.1016/j.cclet.2024.109807
15. [15]
  Wu-Jian Long , Yang Yu , Chuang He . A novel and promising engineering application of carbon dots: Enhancing the chloride binding performance of cement. Chinese Chemical Letters, 2024, 35(6): 108943-. doi: 10.1016/j.cclet.2023.108943
16. [16]
  Bo Yang , Pu-An Lin , Tingwei Zhou , Xiaojia Zheng , Bing Cai , Wen-Hua Zhang . Facile surface regulation for highly efficient and thermally stable perovskite solar cells via chlormequat chloride. Chinese Chemical Letters, 2024, 35(10): 109425-. doi: 10.1016/j.cclet.2023.109425
17. [17]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
18. [18]
  Haiming Wu , Gaya N. Andrew , Rajini Anumula , Zhixun Luo . Corrigendum to 'How ligand coordination and superatomic-states accommodate the structure and property of a metal cluster: Cu₄ (dppy)₄ Cl₂ vs. Cu₂₁ (dppy)₁₀ with altered photoluminescence' [Chin. Chem. Lett. 35 (2024) 108340]. Chinese Chemical Letters, 2024, 35(12): 109912-. doi: 10.1016/j.cclet.2024.109912
19. [19]
  Jiao Wang , Shuang-Yan Lang , Zhen-Zhen Shen , Gui-Xian Liu , Jian-Xin Tian , Yuan Li , Rui-Zhi Liu , Rui Wen . In situ imaging of the interfacial processes manipulated by salt concentration on zinc anodes in zinc metal batteries. Chinese Chemical Letters, 2025, 36(4): 109815-. doi: 10.1016/j.cclet.2024.109815
20. [20]
  Yanbing Shen , Yuan Yuan , Yaxin Wang , Xiaonan Ma , Wensheng Yang , Yulan Chen . Dihydroanthracene bridged bis-naphthopyrans: A multimodal chromophore with mechano- and photo-chromic properties. Chinese Chemical Letters, 2024, 35(5): 108949-. doi: 10.1016/j.cclet.2023.108949

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(304)
HTML views(9)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142