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Manipulating γ-cyclodextrin-mediated photocyclodimerization of anthracenecarboxylate by wavelength, temperature, solvent and host

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Abstract

Wavelength effects on the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate (AC) mediated by native and modified γ-cyclodextrins (CDs) were examined in different solvents at varying temperatures to manipulate the photochirogenic outcomes beyond the thermodynamically determined re/ si-enantiotopic face selectivity upon 2:1 complexation of AC with CD in the ground state. Indeed, the stereochemical outcomes, i.e. syn/ anti, head-to-tail/ head-to-head (HT/HH) and in particular enantiomer ratios, were critical functions of the irradiation wavelength, irrespective of the CD host employed. Furthermore, the wavelength effects observed strongly depended on the host structure, reaction temperature and solvent employed, for which altered stacking geometry of the complexed AC pair is thought to be responsible. By optimizing the irradiation wavelength, chiral host, temperature and solvent, an enantiomeric excess of up to 54 and −37% were achieved for chiral syn-HT and anti-HH dimers.

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Authors and Affiliations

  1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, China

    Cheng Yang & Jabing Yao

  2. Department of Applied Chemistry, Osaka University, Yamada-oka 2-1, Suita 565-0871, Japan

    Qian Wang, Masahito Yamauchi, Gaku Fukuhara, Tadashi Mori & Yoshihisa Inoue

  3. Department of Chemistry and State Key Laboratory of Elemento-Organic Chemistry, Nankai University Tianjin, 30071, China

    Qian Wang & Yu Liu

  4. Comprehensive Analysis Center, ISIR, Mihogaoka, Ibaraki 567-0047, Japan

    Dayang Zhou

  5. Office for University-Industry Collaboration, Osaka University, Yamada-oka 2-8, Suita, 565-0871, Japan

    Masaki Nishijima

Authors
  1. Cheng Yang
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  2. Qian Wang
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  3. Masahito Yamauchi
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  5. Dayang Zhou
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  7. Gaku Fukuhara
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  8. Tadashi Mori
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  9. Yu Liu
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  10. Yoshihisa Inoue
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Corresponding authors

Correspondence to Cheng Yang, Yu Liu or Yoshihisa Inoue.

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This paper is dedicated to the memory of Prof. Nicholas Turro.

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Yang, C., Wang, Q., Yamauchi, M. et al. Manipulating γ-cyclodextrin-mediated photocyclodimerization of anthracenecarboxylate by wavelength, temperature, solvent and host. Photochem Photobiol Sci 13, 190–198 (2014). https://doi.org/10.1039/c3pp50255d

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