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苯乙烯基蒽的波长选择性光环加成反应

Wavelength-Selective Photo-Cycloadditions of Styryl-Anthracene.

作者信息

Bai Jing, Shi Zixing, Ma Xiaodong, Yin Jie, Jiang Xuesong

机构信息

School of Chemistry & Chemical Engineering, Frontiers Science Center for Transformative Molecules, State Key Laboratory for Metal Matrix Composite Materials, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China.

出版信息

Macromol Rapid Commun. 2022 May;43(9):e2200055. doi: 10.1002/marc.202200055. Epub 2022 Apr 7.

Abstract

Light-tunable covalent chemistry is highly urgent in the fields of chemistry, biology, and materials science, especially for the smart materials and surface, due to the spatiotemporal control and feasible operation. Here, a new type of wavelength-selective photo-cycloaddition of styryl-anthracene carboxylic acid (SACA) is reported. Upon the irradiation of 450 nm visible light or 365 nm UV light, SACA can undergo [2+2] or [2+4] photocycloaddition, respectively. Furthermore, the [2+2] photocycloaddition induced by vis-light of 450 nm is reversible and can be disrupted by 365 nm UV light to form dimer-24 which cannot be photo-cleavable. Owing to the feasibility and spatiotemporal characteristics of UV-vis light-controlled photocycloaddition, the SACA possesses potential applications in various areas such as self-assembly, dynamic wrinkles, and fluorescence patterns, which are also explored and exhibited in this work.

摘要

由于具有时空控制和可行的操作,光可调共价化学在化学、生物学和材料科学领域非常迫切,特别是对于智能材料和表面。在此,报道了一种新型的苯乙烯基蒽羧酸(SACA)的波长选择性光环加成反应。在450nm可见光或365nm紫外光照射下,SACA可分别发生[2+2]或[2+4]光环加成反应。此外,450nm可见光诱导的[2+2]光环加成反应是可逆的,可被365nm紫外光破坏形成不可光裂解的二聚体-24。由于紫外-可见光控制的光环加成反应具有可行性和时空特性,SACA在自组装、动态皱纹和荧光图案等各个领域具有潜在应用,本文也对其进行了探索和展示。

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