Diazocine Derivatives: A Family of Azobenzenes for Photochromism with Highly Enhanced Turn-On Fluorescence

Qian Zhu; Suning Wang; Pangkuan Chen

doi:10.1021/acs.orglett.9b01215

Diazocine Derivatives: A Family of Azobenzenes for Photochromism with Highly Enhanced Turn-On Fluorescence

Qian Zhu, Suning Wang, Pangkuan Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

Abstract

π-Conjugated azobenzene derivatives were reported to couple azo moieties with aryl fluorophore. Using the photochemistry of the C₂-bridged azobenzene, we have accomplished two diazocine-based photoswitching molecules (cAz1 and cAz2). In addition to remarkable photochromic properties, they show a turn-on fluorescence, and the emission was highly enhanced with quantum efficiency increasing up to 0.22 for cAz1. The emission remains persistent and can only be switched off via thermal deactivation. They display greater optical responses, compared with the linear analogues (Az1-Az4). This work may provide a new scaffold toward advanced light-emitting materials using photoswitchable systems.

Original language	English
Pages (from-to)	4025-4029
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.9b01215
Publication status	Published - 7 Jun 2019

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title = "Diazocine Derivatives: A Family of Azobenzenes for Photochromism with Highly Enhanced Turn-On Fluorescence",

abstract = "π-Conjugated azobenzene derivatives were reported to couple azo moieties with aryl fluorophore. Using the photochemistry of the C2-bridged azobenzene, we have accomplished two diazocine-based photoswitching molecules (cAz1 and cAz2). In addition to remarkable photochromic properties, they show a turn-on fluorescence, and the emission was highly enhanced with quantum efficiency increasing up to 0.22 for cAz1. The emission remains persistent and can only be switched off via thermal deactivation. They display greater optical responses, compared with the linear analogues (Az1-Az4). This work may provide a new scaffold toward advanced light-emitting materials using photoswitchable systems.",

author = "Qian Zhu and Suning Wang and Pangkuan Chen",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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T2 - A Family of Azobenzenes for Photochromism with Highly Enhanced Turn-On Fluorescence

AU - Zhu, Qian

AU - Wang, Suning

AU - Chen, Pangkuan

PY - 2019/6/7

Y1 - 2019/6/7

N2 - π-Conjugated azobenzene derivatives were reported to couple azo moieties with aryl fluorophore. Using the photochemistry of the C2-bridged azobenzene, we have accomplished two diazocine-based photoswitching molecules (cAz1 and cAz2). In addition to remarkable photochromic properties, they show a turn-on fluorescence, and the emission was highly enhanced with quantum efficiency increasing up to 0.22 for cAz1. The emission remains persistent and can only be switched off via thermal deactivation. They display greater optical responses, compared with the linear analogues (Az1-Az4). This work may provide a new scaffold toward advanced light-emitting materials using photoswitchable systems.

AB - π-Conjugated azobenzene derivatives were reported to couple azo moieties with aryl fluorophore. Using the photochemistry of the C2-bridged azobenzene, we have accomplished two diazocine-based photoswitching molecules (cAz1 and cAz2). In addition to remarkable photochromic properties, they show a turn-on fluorescence, and the emission was highly enhanced with quantum efficiency increasing up to 0.22 for cAz1. The emission remains persistent and can only be switched off via thermal deactivation. They display greater optical responses, compared with the linear analogues (Az1-Az4). This work may provide a new scaffold toward advanced light-emitting materials using photoswitchable systems.

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Diazocine Derivatives: A Family of Azobenzenes for Photochromism with Highly Enhanced Turn-On Fluorescence

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