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Supramolecular Photochirogenesis with Cyclodextrin

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Handbook of Macrocyclic Supramolecular Assembly

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Abstract

Supramolecular photochirogenesis is a rapidly growing interdisciplinary area of photochemistry, asymmetric synthesis, and supramolecular chemistry. The cooperative noncovalent interactions and confinement of guest substrate(s) with chiral host in both ground and excited states often enable more efficient chirality transfer in supramolecular assemblies than in isotropic media. In supramolecular photochirogenic reactions, overall chirality control is achieved in multiple steps by: (1) thermodynamically preorganizing photosubstrate(s) in the ground state, (2) spectroscopically differentiating the diastereomeric host-guest complex pair by absorbance, and (3) kinetically manipulating the subsequent chemical transformation in the excited state through the weak but nontransient interactions in the chiral supramolecular environment. Thus, all of the ground- and excited-state properties, including the binding affinity and stoichiometry, the chiroptical and photophysical properties, and the photochemical reactivity, jointly affect the stereochemical outcome of photochirogenic reactions. The less significant role of entropy in the photochemical step, due to the confinement, is another unique property of supramolecular photochirogenesis, when compared with the conventional chiral photochemistry. This chapter deals with the chiral supramolecular photoreactions mediated by native and modified cyclodextrins (CDs), one of the most intensively studied chiral host molecules, and covers uni- and bimolecular photoreactions, catalytic photochirogenesis, as well as the wavelength effects on CD-mediated photoreactions reported by early 2019. We also discuss the advantages of using CDs as chiral hosts for photochirogenesis, the factors and plausible mechanisms that lead to highly stereoselective supramolecular photochirogenesis, the challenges and difficulties in achieving efficient chiral induction through CD-based supramolecular photochirogenic systems, and finally the conclusions and the future perspective of this multidisciplinary research field.

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Acknowledgments

We acknowledge the support of this work by the National Natural Science Foundation of China (No. 21871194, 21572142, 21372165, 21402129 and 21402110), the National Key Research and Development Program of China (No. 2017YFA0505903), and the Science & Technology Department of Sichuan Province (2019YJ0160, 2019YJ0090, 2017SZ0021).

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Authors and Affiliations

  1. Sichuan University, Chengdu, China

    Jiabin Yao & Cheng Yang

  2. Osaka University, Suita, China

    Yoshihisa Inoue

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  1. Jiabin Yao
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  2. Yoshihisa Inoue
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  3. Cheng Yang
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Correspondence to Yoshihisa Inoue or Cheng Yang .

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Editors and Affiliations

  1. College of Chemistry, Nankai University College of Chemistry, Tianjin, Tianjin, China

    Yu Liu

  2. College of Chemistry, Nankai University College of Chemistry, Tianjin, Tianjin, China

    Yong Chen

  3. College of Chemistry, Nankai University College of Chemistry, Tianjin, Tianjin, China

    Heng-Yi Zhang

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Yao, J., Inoue, Y., Yang, C. (2019). Supramolecular Photochirogenesis with Cyclodextrin. In: Liu, Y., Chen, Y., Zhang, HY. (eds) Handbook of Macrocyclic Supramolecular Assembly . Springer, Singapore. https://doi.org/10.1007/978-981-13-1744-6_20-1

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