Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 11, Pages 2874-2878Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201713387
Keywords
arenes; cell death; chromophores; fluorescence; polycycles; warped nanographenes
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Funding
- ERATO program from JST [JPMJER1302]
- Funding Program for KAKENHI from MEXT [JP16K05771]
- JSPS [JP16H06464, JP16H06280, JP17H05149]
- US National Science Foundation [CHE-1149096]
- World Premier International Research Center Initiative (WPI), Japan
- Grants-in-Aid for Scientific Research [16K05771] Funding Source: KAKEN
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Nanographene, a small piece of graphene, has attracted unprecedented interest across diverse scientific disciplines particularly in organic electronics. The biological applications of nanographenes, such as bioimaging, cancer therapies and drug delivery, provide significant opportunities for breakthroughs in the field. However, the intrinsic aggregation behavior and low solubility of nanographenes, which stem from their flat structures, hamper their development for bioapplications. Herein, we report a water-soluble warped nanographene (WNG) that can be easily synthesized by sequential regioselective C-H borylation and cross-coupling reactions of the saddle-shaped WNG core structure. The saddle-shaped structure and hydrophilic tetraethylene glycol chains impart high water solubility to the WNG. The watersoluble WNG possesses a range of promising properties including good photostability and low cytotoxicity. Moreover, the water-soluble WNG was successfully internalized into HeLa cells and promoted photoinduced cell death.
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