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A Water‐Soluble Warped Nanographene: Synthesis and Applications for Photoinduced Cell Death
Author(s) -
Lin HsingAn,
Sato Yoshikatsu,
Segawa Yasutomo,
Nishihara Taishi,
Sugimoto Nagisa,
Scott Lawrence T.,
Higashiyama Tetsuya,
Itami Kenichiro
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713387
Subject(s) - nanotechnology , materials science , solubility , graphene , combinatorial chemistry , chemistry , organic chemistry
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 water‐soluble 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.