Citation: Lu Yanluo, Tang Yanqun, Lin Heyang, Fang Xiaoyu, Lu Bo, Li Dan, Yan Dongpeng. Selective formation of luminescent chiral cocrystal: Molecular self-assembly of 2, 2'-binaphthol and 2-(3-pyridyl)-1H-benzimidazole[J]. Chinese Chemical Letters, ;2018, 29(10): 1541-1543. doi: 10.1016/j.cclet.2017.12.021 shu

Selective formation of luminescent chiral cocrystal: Molecular self-assembly of 2, 2'-binaphthol and 2-(3-pyridyl)-1H-benzimidazole

Lu Yanluo ^a ,
Tang Yanqun ^a ,
Lin Heyang ^a ,
Fang Xiaoyu ^b ,
Lu Bo ^b ,
Li Dan ^b ,
Yan Dongpeng ^a,b,,

a.
State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China
b.
Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China

Corresponding author: Yan Dongpeng, yandongpeng001@163.com
Received Date: 22 November 2017
Revised Date: 22 January 2018
Accepted Date: 22 January 2018
Available Online: 28 October 2017

Figures(7)

Luminescent cocrystals have been received much attention in fluorescence imaging and sensor application. In this work, we report that the high-quality chiral luminescent cocrystal can be obtained through a molecular self-assembly process of 2, 2'-binaphthol and 2-(3-pyridyl)-1H-benzimidazole. The assembly modes and stacking fashions of as-obtained cocrystal were determined by single crystal X-ray diffractometer. The structure and optical properties of the cocrystals were characterized by fluorescence emission, fluorescence decay, Raman and circular dichroism spectra. The results show that both the pristine co-assembled units (R-BINOL and S-BINOL) give rise to the R conformation within the final cocrystal, suggesting that the formation of cocrystal can be an effective way to achieve R/S-isomeric transformation of 2, 2'-binaphthol. It is also expected that the co-crystallization approach has much flexibility and potential applications for the design and selective formation of chiral luminescent materials.
- Chiral cocrystal,
- Molecular self-assembly,
- Binaphthol
1. [1]
  R. Noyori, Chem. Soc. Rev. 18(1989) 187-208. doi: 10.1039/cs9891800187
2. [2]
  J. Wilting, M. Janssen, C. Muller, et al., Adv. Synth. Catal. 349(2007) 350-356. doi: 10.1002/(ISSN)1615-4169
3. [3]
  F.Y. Jiang, B. Liu, Z.B. Dong, et al., J. Organomet. Chem. 692(2007) 4377-4380. doi: 10.1016/j.jorganchem.2007.07.003
4. [4]
  J.M. Brunel, Chem. Rev. 105(2005) 857-897. doi: 10.1021/cr040079g
5. [5]
  X. Fang, X. Yang, D. Yan, J. Mater. Chem. C 5(2017) 1632-1637. doi: 10.1039/C6TC05048D
6. [6]
  G. Fan, D. Yan, Adv. Opt. Mater. 4(2016) 2139-2147. doi: 10.1002/adom.v4.12
7. [7]
  G. Fan, X. Yang, R. Liang, et al., CrystEngComm 18(2016) 240-249. doi: 10.1039/C5CE02019K
8. [8]
  S. Li, Y. Lin, D. Yan, J. Mater. Chem. C 4(2016) 2527-2534. doi: 10.1039/C6TC00067C
9. [9]
  D. Yan, B. Patel, A. Delori, et al., Cryst. Growth Des. 13(2013) 333-340.
10. [10]
  D. Yan, Y. Lin, Q. Meng, et al., Cryst. Growth Des. 13(2013) 4495-4503. doi: 10.1021/cg400979d
11. [11]
  G. Bruni, M. Maietta, V. Berbenni, et al., J. Phys. Chem. B 118(2014) 9180-9190. doi: 10.1021/jp503256k
12. [12]
  D. Yan, H. Yang, Q. Meng, et al., Adv. Funct. Mater. 24(2014) 587-594. doi: 10.1002/adfm.201302072
13. [13]
  D. Yan, D.G. Evans, Mater. Horiz. 1(2014) 46-57. doi: 10.1039/C3MH00023K
14. [14]
  O. Sánchez-Guadarrama, F. Mendoza-Navarro, A. Cedillo-Cruz, et al., Cryst. Growth Des. 16(2016) 307-314. doi: 10.1021/acs.cgd.5b01254
15. [15]
  R. Pummerer, E. Prell, A. Rieche, Ber. Dtsch. Chem. Ges. 59(1926) 2159-2161. doi: 10.1002/cber.19260590881
16. [16]
  R. Noyori, I. Tomino, Y. Tanimoto, J. Am. Chem. Soc. 101(1979) 3129-3131. doi: 10.1021/ja00505a056
1. [1]
  Junjie Duan , Dan Chen , Long Chen , Shuying Li , Ting Chen , Dong Wang . 2D hexagonal tessellations sustained by Br···Br/H contacts: From regular to semiregular to k-uniform tilings. Chinese Chemical Letters, 2025, 36(3): 110445-. doi: 10.1016/j.cclet.2024.110445
2. [2]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
3. [3]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
4. [4]
  Fadeng Yang , Pengli Zhang , Jianbo Liu , Chuan Wan , Jinming Sun , Chuan Dai , Zhihong Liu , Yuhao An , Yujie Wu , Yun Xing , Feng Yin , Yuxin Ye , Wei Han , Zigang Li . Self-assembly of a cyclo-pentapeptide with a novel frame structure. Chinese Chemical Letters, 2025, 36(9): 110785-. doi: 10.1016/j.cclet.2024.110785
5. [5]
  Bin Yao , Yao Bu , Hongfei Sun , Guowang Li , Xianying Wu , Wei Wang . Interlocked covalent organic cages: Design, synthesis, and self-assembly. Chinese Chemical Letters, 2026, 37(1): 111894-. doi: 10.1016/j.cclet.2025.111894
6. [6]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
7. [7]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
8. [8]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
9. [9]
  Changlin Su , Wensheng Cai , Xueguang Shao . Water as a probe for the temperature-induced self-assembly transition of an amphiphilic copolymer. Chinese Chemical Letters, 2025, 36(4): 110095-. doi: 10.1016/j.cclet.2024.110095
10. [10]
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11. [11]
  Ming-Ming Gan , Zi-En Zhang , Xin Li , F. Ekkehardt Hahn , Ying-Feng Han . Hierarchical self-assembly of fluorinated poly-N-heterocyclic carbene pillarplexes with anions. Chinese Chemical Letters, 2025, 36(10): 110624-. doi: 10.1016/j.cclet.2024.110624
12. [12]
  Ying Zhao , Yao He , Jian-Xin Yang , Wen-Jie Liu , Dan Tian , Francisco Aznarez , Le-Le Gong , Li-Long Dang , Lu-Fang Ma . Controllable self-assembly and photothermal conversion of metalla[2]catenanes induced by synergistic effect of free radicals and stacking interactions. Chinese Chemical Letters, 2025, 36(12): 111460-. doi: 10.1016/j.cclet.2025.111460
13. [13]
  Ya-Jie Zhu , Zhi-Min Lv , Hao-Feng Zhu , Qi-Yan Qi , Shang-Bo Yu , Jia Tian , Wei Zhou , Zhan-Ting Li . Self-assembly of disassemblable supramolecular organic frameworks for doxorubicin delivery, photofrin posttreatment phototoxicity inhibition and heparin neutralization. Chinese Chemical Letters, 2026, 37(1): 111353-. doi: 10.1016/j.cclet.2025.111353
14. [14]
  Xing-Cheng Hu , Qiu-Shui Mu , Shu-Jin Bao , Yan Zou , Xin-Yu Wang , Guo-Xin Jin . Ligand conformational adaptability modulated self-assembly of Solomon links (412) and trefoil knots (31). Chinese Journal of Structural Chemistry, 2025, 44(10): 100712-100712. doi: 10.1016/j.cjsc.2025.100712
15. [15]
  Linlin Gan , Xuan Peng , Wenchao Zhai , Cheng Zhang , Xinyu Duan , Ke Deng , Wei Li , Qingdao Zeng . Regulatory effects of coronene and pyridine on the self-assembly structure of tetracarboxylic acid derivative formed by dimeric building blocks. Chinese Chemical Letters, 2026, 37(3): 110667-. doi: 10.1016/j.cclet.2024.110667
16. [16]
  Ze Cao , Chenqi Ge , Yating Wu , Hua Tang , Yueyan Kuang , Yuyang Wu , Hao Li . Self-assembled chiral cages for anion recognition. Chinese Chemical Letters, 2026, 37(3): 111554-. doi: 10.1016/j.cclet.2025.111554
17. [17]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
18. [18]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
19. [19]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
20. [20]
  Jinchen Li , Tangxin Xiao , Kai Diao , Zhouyu Wang , Leyong Wang . Supramolecular catalysis enabled by chiral molecular cages with anion-π interaction capability. Chinese Chemical Letters, 2026, 37(1): 111796-. doi: 10.1016/j.cclet.2025.111796

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