Citation: Cheng Yang. Recent progress in supramolecular chiral photochemistry[J]. Chinese Chemical Letters, ;2013, 24(6): 437-441. shu

Recent progress in supramolecular chiral photochemistry

Cheng Yang ^,

1.
College of Chemistry, Sichuan University, Chengdu 610064, China

Corresponding author: Cheng Yang,
Received Date: 25 February 2013
Available Online: 14 March 2013

Chiral photochemistry appears to be a highly challenging topic and still very much in its infancy, especially if comparing to its well-developed thermochemical counterpart. Significant efforts have been devoted in order to improve stereoselectivity of chiral photoreactions, among which, the supramolecular strategy proven the most promising. The present review, motivated by the rapid progress in the supramolecular chiral photochemistry, concentrates on advancements achieved mainly in the last decade. The features and advantages of supramolecular chiral photochemistry are exemplified by representative photoreactions in terms of the chiral hosts/assemblies.
- Supramolecular chemistry,
- Photochemistry,
- Stereochemistry,
- Photochirogenesis
1. [1]
  [1] E.L. Eliel, S.H. Wilen, Topics in Stereochemistry, Wiley-Interscience, 2009.
2. [2]
  [2] Y. Inoue, V. Ramamurthy, Chiral Photochemistry, Marcel Dekker, New York, 2004.
3. [3]
  [3] Y. Inoue, T. Wada, N. Sugahara, et al., Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins, J. Org. Chem. 65 (2000) 8041-8050.
4. [4]
  [4] R. Lu, C. Yang, Y. Cao, et al., Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by aroyl-β-cyclodextrins: a critical enantioselectivity control by substituents, J. Org. Chem. 73 (2008) 7695-7701.
5. [5]
  [5] C. Yang, T. Mori, T. Wada, Y. Inoue, Supramolecular enantiodifferentiating photoisomerization of (Z,Z)-1,3-cyclooctadiene included and sensitized by naphthalene-modified cyclodextrins, New J. Chem. 31 (2007) 697-702.
6. [6]
  [6] T. Tamaki, T. Kokubu, Acceleration of the photodimerization of water-soluble anthracenes included by b and γ-cyclodextrins, J. Incl. Phenom. Macro. 2 (1984) 815-821.
7. [7]
  [7] A. Nakamura, Y. Inoue, Supramolecular catalysis of the enantiodifferentiating[4+4] photocyclodimerization of 2-anthracenecarboxylate by g-cyclodextrin, J. Am. Chem. Soc. 125 (2003) 966-974.
8. [8]
  [8] C. Yang, G. Fukuhara, A. Nakamura, et al., Enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate catalyzed by 6A,6X-diamino-6A,6X-dideoxy-γ-cyclodextrins: manipulation of product chirality by electrostatic interaction, temperature and solvent in supramolecular photochirogenesis, J. Photochem. Photobiol. A: Chem. 173 (2005) 375-384.
9. [9]
  [9] H. Ikeda, T. Nihei, A. Ueno, Template-assisted stereoselective photocyclodimerization of 2-anthracenecarboxylic acid by bispyridinio-appended gamma-cyclodextrin, J. Org. Chem. 70 (2005) 1237-1242.
10. [10]
  [10] C. Yang, T. Mori, Y. Inoue, Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by capped γ-cyclodextrins: critical control of enantioselectivity by cap rigidity, J. Org. Chem. 73 (2008) 5786-5794.
11. [11]
  [11] C. Yang, T. Mori, Y. Origane, et al., Highly stereoselective photocyclodimerization of a-cyclodextrin-appended anthracene mediated by g-cyclodextrin and cucurbit[8]uril: a dramatic steric effect operating outside the binding site, J. Am. Chem. Soc. 130 (2008) 8574-8575.
12. [12]
  [12] C. Yang, C. Ke, W. Liang, et al., Dual supramolecular photochirogenesis: ultimate stereocontrol of photocyclodimerization by a chiral scaffold and confining host, J. Am. Chem. Soc. 133 (2011) 13786-13789.
13. [13]
  [13] L. Luo, G.H. Liao, X.L. Wu, L. Lei, C.H. Tung, L.Z. Wu, γ-Cyclodextrin-directed enantioselective photocyclodimerization of methyl 3-methoxyl-2-naphthoate, J. Org. Chem. 74 (2009) 3506-3515.
14. [14]
  [14] L. Luo, S.F. Cheng, B. Chen, C.H. Tung, L.Z.Wu, Stepwise photochemical-chiral delivery in g-cyclodextrin-directed enantioselective photocyclodimerization of methyl 3-methoxyl-2-naphthoate in aqueous solution, Langmuir 26 (2010) 197-249.
15. [15]
  [15] W. Liang, H.H. Zhang, J.J. Wang, et al., Supramolecular complexation and photocyclodimerization of methyl 3-methoxy-2-naphthoate with modified cyclodextrins, Pure Appl. Chem. 83 (2011), 769-768.
16. [16]
  [16] T. Bach, H. Bergmann, H. Brummerhop, W. Lewis, K. Harms, The [2+2]-photocycloaddition of aromatic aldehydes and ketones to 3,4-dihydro-2-pyridones: regioselectivity, diastereoselectivity, and reductive ring opening of the product oxetanes, Chem. Eur. J. 7 (2001) 4512.
17. [17]
  [17] T. Bach, H. Bergmann, B. Grosch, K. Harms, Highly enantioselective intra- and intermolecular [2+2] photocycloaddition reactions of 2-quinolones mediated by a chiral lactam host: host-guest interactions, product configuration, and the origin of the stereoselectivity in solution, J. Am. Chem. Soc. 124 (2002) 7982-7983.
18. [18]
  [18] A. Bauer, F. Westkämper, S. Grimme, T. Bach, Catalytic enantioselective reactions driven by photoinduced electron transfer, Nature 436 (2005) 1139-1140.
19. [19]
  [19] S. Breitenlechner, T. Bach, A polymer-bound chiral template for enantioselective photochemical reactions, Angew. Chem. Inter. Ed. 47 (2008) 7957-7959.
20. [20]
  [20] Y. Kawanami, T.C.S. Pace, J.I. Mizoguchi, et al., Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates, J. Org. Chem. 74 (2009) 7908-7921.
21. [21]
  [21] T. Wada, N. Sugahara, M. Kawano, Y. Inoue, First asymmetric photochemistry with nucleosides and DNA: enantiodifferentiating Z-E photoisomerization of cyclooctene, Chem. Lett. (2000) 1174-1175.
22. [22]
  [22] M. Nishijima, T.C.S. Pace, A. Nakamura, et al., Supramolecular photochirogenesis with biomolecules. Mechanistic studies on the enantiodifferentiation for the photocyclodimerization of 2-anthracenecarboxylate mediated by bovine serum albumin, J. Org. Chem. 72 (2007) 2707-2713.
23. [23]
  [23] K. Bando, T. Zako, M. Sakono, et al., Bio-supramolecular photochirogenesis with molecular chaperone: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by prefoldin, Photochem. Photobiol. Sci. 9 (2010) 655-660.
24. [24]
  [24] Y. Ishida, Y. Kai, S.Y. Kato, et al., Two-component liquid crystals as chiral reaction media: highly enantioselective photodimerization of an anthracene derivative driven by the ordered microenvironment, Angew. Chem. Inter. Ed. 47 (2008) 8241-8245.
25. [25]
  [25] F.F. Lv, B. Chen, L.Z. Wu, L.P. Zhang, C.H. Tung, Enhanced stereoselectivity in photoelectrocyclization of tropolone ethers via confinement in chiral inductormodified lyotropic liquid crystals, Org. Lett. 10 (2008) 3473-3476.
26. [26]
  [26] A. Dawn, T. Shiraki, S. Haraguchi, et al., Transcription of chirality in the organogel systems dictates the enantiodifferentiating photodimerization of substituted anthracene, Chem. A Eur. J. 16 (2010) 3676-3689.
27. [27]
  [27] Y. Nishioka, T. Yamaguchi, M. Kawano, M. Fujita, Asymmetric [2+2] olefin cross photoaddition in a self-assembled host with remote chiral auxiliaries, J. Am. Chem. Soc. 130 (2008) 8160-8161.
1. [1]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
2. [2]
  Chao Zhang , Ai-Feng Liu , Shihui Li , Fang-Yuan Chen , Jun-Tao Zhang , Fang-Xing Zeng , Hui-Chuan Feng , Ping Wang , Wen-Chao Geng , Chuan-Rui Ma , Dong-Sheng Guo . A supramolecular formulation of icariin@sulfonatoazocalixarene for hypoxia-targeted osteoarthritis therapy. Chinese Chemical Letters, 2025, 36(1): 109752-. doi: 10.1016/j.cclet.2024.109752
3. [3]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
4. [4]
  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
5. [5]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
6. [6]
  Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
7. [7]
  Zhiwei Zhong , Yanbin Huang , Wantai Yang . A simple photochemical method for surface fluorination using perfluoroketones. Chinese Chemical Letters, 2024, 35(5): 109339-. doi: 10.1016/j.cclet.2023.109339
8. [8]
  Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
9. [9]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
10. [10]
  Kang Wei , Jiayu Li , Wen Zhang , Bing Yuan , Ming-De Li , Pingwu Du . A strained π-extended [10]cycloparaphenylene carbon nanoring. Chinese Chemical Letters, 2024, 35(5): 109055-. doi: 10.1016/j.cclet.2023.109055
11. [11]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
12. [12]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
13. [13]
  Zixi Zou , Jingyuan Wang , Yian Sun , Qian Wang , Da-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972
14. [14]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
15. [15]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
16. [16]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
17. [17]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
18. [18]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
19. [19]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
20. [20]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(620)
HTML views(1)

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