Photoinduced Fluorescence Switching in Molecular Aggregates by Topological [2+2] Cycloaddition

Author:

Pan Guocui1,Wu Zhiyuan1,Liu Zhaoyang1,Xu Bin1ORCID,Tian Wenjing1

Affiliation:

1. State Key Laboratory of Supramolecular Structure and Materials College of Chemistry Jilin University Qianjin Street No. 2699 Changchun 130012 China

Abstract

AbstractThe optical modulation of fluorescence characteristics in molecular aggregates, which mainly involves diverse molecular stacking and the consequent intermolecular interactions, remains a significant challenge for potential applications in optical anticounterfeiting, data storage, and imaging. Here we successfully realize in situ fluorescence switching in molecular aggregates of thianaphthene‐dioxide derivatives by topological [2+2] photocycloaddition, which represents a promising way to regulate the molecular stacking and alter photophysical processes. Notably, 2‐(3,5‐bis‐trifluoromethylphenyl)benzo[b]thiophene‐dioxide (BTO‐TF) in both crystal and powder forms exhibits a unique switching from an initial nonfluorescent state to a highly fluorescent state (ΦPL=0.46) upon UV irradiation, because of the destruction of the [2+2] cycloaddition process by volume expansion of the photodimer. Furthermore, we demonstrate such a [2+2] photocycloaddition can occur when 2‐(4‐carboxypheny)benzo[b]thiophene‐dioxide (BTO‐OH) is doped within selective polymer matrixes, and can be utilized for the visualization of macrophase separation in polymer blends.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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