Aziridinyl Fluorophores Demonstrate Bright Fluorescence and Superior Photostability by Effectively Inhibiting Twisted Intramolecular Charge Transfer

详细信息    查看全文

• 作者：Xiaogang Liu ; Qinglong Qiao ; Wenming Tian ; Wenjuan Liu ; Jie Chen ; Matthew J. Lang ; Zhaochao Xu
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：June 8, 2016
• 年：2016
• 卷：138
• 期：22
• 页码：6960-6963
• 全文大小：360K
• 年卷期：0
• ISSN：1520-5126

文摘

Replacing conventional dialkylamino substituents with a three-membered aziridine ring in naphthalimide leads to significantly enhanced brightness and photostability by effectively suppressing twisted intramolecular charge transfer formation. This replacement is generalizable in other chemical families of fluorophores, such as coumarin, phthalimide, and nitrobenzoxadiazole dyes. In highly polar fluorophores, we show that aziridinyl dyes even outperform their azetidinyl analogues in aqueous solution. We also proposed one simple mechanism that can explain the vulnerability of quantum yield to hydrogen bond interactions in protonic solvents in various fluorophore families. Such knowledge is a critical step toward developing high-performance fluorophores for advanced fluorescence imaging.