Unveiling how intramolecular stacking modes of covalently linked dimers dictate photoswitching properties

Ru-Qiang Lu, Xiao-Yun Yan, Lei Zhu, Lin-Lin Yang, Hang Qu, Xin-Chang Wang, Ming Luo, Yu Wang, Rui Chen, Xiao-Ye Wang (), Yu Lan (), Jian Pei, Wengui Weng, Haiping Xia and Xiao-Yu Cao ()
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Ru-Qiang Lu: Xiamen University
Xiao-Yun Yan: Xiamen University
Lei Zhu: Chongqing University
Lin-Lin Yang: Xiamen University
Hang Qu: Xiamen University
Xin-Chang Wang: Xiamen University
Ming Luo: Xiamen University
Yu Wang: Xiamen University
Rui Chen: Xiamen University
Xiao-Ye Wang: Nankai University
Yu Lan: Chongqing University
Jian Pei: Peking University
Wengui Weng: Xiamen University
Haiping Xia: Xiamen University
Xiao-Yu Cao: Xiamen University

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract Covalently linked π-stacked dimers represent the most significant platform for elucidating the relationship between molecular alignments and their properties. Here, we present the one-pot synthesis of two intramolecularly π-stacked dimers and disclose how intramolecular stacking modes dictate photoswitching properties. The dimer, which features cofacially stacked chromophores and geometrically favours intramolecular photochemical [2 + 2] cycloadditions, displays a nearly irreversible photoswitching behaviour. By contrast, the dimer, bearing crosswise stacked chromophores, is geometrically unfavourable for the cycloaddition and exhibits a highly reversible photoswitching process, in which the homolysis and reformation of carbon−carbon single bonds are involved. Moreover, the chiral carbon centres of both dimers endow these photoswitches with chirality and the separated enantiomers exhibit tuneable chiroptical properties by photoswitching. This work reveals that intramolecular stacking modes significantly influence the photochemical properties of π-stacked dimers and offers a design strategy toward chiral photoswitchable materials.

Date: 2019
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DOI: 10.1038/s41467-019-13428-3

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