Water-soluble doubly-strapped isolated perylene diimide chromophore

• Main Authors: Yang, Fei, Li, Ran, Wei, Wei, Ding, Xingwei, Xu, Zhenzhen, Wang, Ping, Wang, Guo, Xu, Yanqing, Fu, Hongbing, Zhao, Yanli
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2022
• Subjects: Science::Chemistry; Cyclophanes; Photothermal Conversion
• Online Access: https://hdl.handle.net/10356/162220
• Institution: Nanyang Technological University

Perylene diimides (PDIs), a well-studied class of organic dyes, have a strong tendency to self-aggregate in water, thus greatly restricting their phototheranostic applications. Herein, we report a water-soluble PDI cyclophane "Gemini Box" (GBox-14+ ), consisting of a central PDI chromophore enclosed by double-sided cationic molecular straps. Owing to the effective spatial isolation, the chromophore self-aggregation can be completely eliminated, even in a concentrated aqueous solution up to 2 mM. To our knowledge, GBox-14+ represents an interesting example of a fluorescent PDI cyclophane in water, capable of being employed for lysosome-targetable live-cell imaging. More importantly, the highly concentrated aqueous solution of PDI radical anion can be significantly stabilized by GBox-14+ to exhibit an excellent near-infrared photothermal effect, which was further exploited for efficient and selective antibacterial applications. This work provides a new access to water-soluble non-aggregated organic dyes and promotes their potential biomedical applications.