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Efficient synthesis of cyclic amidine-based fluorophores via 6π-electrocyclic ring closure.

ABSTRACT: Novel 10π-electron cyclic amidines with excellent fluorescence properties were synthesized by a general and efficient 6π-electrocyclic ring closure of ketenimine and imine starting from N-sulfonyl triazoles and arylamines. The photophysical properties of cyclic amidine fluorophores have been studied in detail and have shown good properties of a large Stokes shift, pH insensitivity, low cytotoxicity and higher photostability, which have great potential for biological imaging. Furthermore, this novel fluorophore was successfully applied to the localization of the NK-1 receptor in living systems.

SUBMITTER: Li G

PROVIDER: S-EPMC8152618 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Efficient synthesis of cyclic amidine-based fluorophores <i>via</i> 6π-electrocyclic ring closure.

Li Guofeng G Zhao Man M Xie Junqiu J Yao Ying Y Mou Lingyun L Zhang Xiaowei X Guo Xiaomin X Sun Wangsheng W Wang Zheng Z Xu Jiecheng J Xue Jianzhong J Hu Tao T Zhang Ming M Li Min M Hong Liang L

Chemical science 20200313 14

Novel 10π-electron cyclic amidines with excellent fluorescence properties were synthesized by a general and efficient 6π-electrocyclic ring closure of ketenimine and imine starting from <i>N</i>-sulfonyl triazoles and arylamines. The photophysical properties of cyclic amidine fluorophores have been studied in detail and have shown good properties of a large Stokes shift, pH insensitivity, low cytotoxicity and higher photostability, which have great potential for biological imaging. Furthermore, ...[more]

PMID: 34094046

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