General Principles for the Design of Visible‐Light‐Responsive Photoswitches: Tetra‐ortho‐Chloro‐Azobenzenes,Angewandte Chemie International Edition

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General Principles for the Design of Visible‐Light‐Responsive Photoswitches: Tetra‐ortho‐Chloro‐Azobenzenes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-08-17 , DOI: 10.1002/anie.202008700
Lucien N Lameijer _{1,

2} , Simon Budzak ₃ , Nadja A Simeth ₂ , Mickel J Hansen ₂ , Ben L Feringa ₂ , Denis Jacquemin ₄ , Wiktor Szymanski _{1,

2}

Affiliation

Molecular photoswitches enable reversible external control of biological systems, nanomachines, and smart materials. Their development is driven by the need for low energy (green‐red‐NIR) light switching, to allow non‐invasive operation with deep tissue penetration. The lack of clear design principles for the adaptation and optimization of such systems limits further applications. Here we provide a design rulebook for tetra‐ortho‐chloroazobenzenes, an emerging class of visible‐light‐responsive photochromes, by elucidating the role that substituents play in defining their key characteristics: absorption spectra, band overlap, photoswitching efficiencies, and half‐lives of the unstable cis isomers. This is achieved through joint photochemical and theoretical analyses of a representative library of molecules featuring substituents of varying electronic nature. A set of guidelines is presented that enables tuning of properties to the desired application through informed photochrome engineering.

中文翻译：

可见光响应光电开关设计的一般原则：四邻氯偶氮苯

分子光电开关能够对生物系统、纳米机器和智能材料进行可逆的外部控制。它们的发展是由低能量（绿-红-近红外）光开关的需求驱动的，以允许进行深层组织穿透的非侵入性操作。缺乏明确的设计原则来适应和优化此类系统限制了进一步的应用。在这里，我们通过阐明取代基在定义其关键特性（吸收光谱、带重叠、光开关效率和半衰期）中所起的作用，提供了四邻氯偶氮苯（一类新兴的可见光响应光致变色材料）的设计规则手册不稳定的顺式异构体。这是通过对具有不同电子性质的取代基的代表性分子库进行联合光化学和理论分析来实现的。提出了一组指南，可以通过知情的光致变色工程将性能调整到所需的应用。

更新日期：2020-08-17

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