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Near‐Infrared‐Emitting Nitrogen‐Doped Nanographenes
Author(s) -
Yamato Kairi,
Sekiya Ryo,
Suzuki Kaho,
Haino Takeharu
Publication year - 2019
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.201901510
Subject(s) - photoluminescence , photochemistry , doping , chemistry , infrared , near infrared spectroscopy , absorption (acoustics) , materials science , derivative (finance) , optoelectronics , optics , physics , financial economics , economics , composite material
The quantum‐size effect, which enables nanographenes to emit photoluminescence (PL) in the UV to visible region, has inspired intense research. However, the control of the PL properties of nanographenes through manipulation of their π‐system by post‐modifications is not well developed. By utilizing a ring‐closure reaction between an aromatic 1,2‐dicarboxylic acid and a 1,8‐naphthalenediamine derivative, which produces a perimidine framework, nitrogen‐doped nanographenes were realized. Two nanographenes produced by a one‐pot reaction of edge‐oxidized nanographene (GQD‐ 2 ) with 1,8‐naphthalenediamine derivatives (GQD‐ 1 a and GQD‐ 1 b ) displayed an absorption band extending to >1000 nm; furthermore, the PL wavelength of GQD‐ 1 a was significantly red‐shifted into the near‐infrared (NIR) region in which it can be used for bioimaging. Time‐dependent DFT calculations of model nanographenes showed that the functional groups narrow the HOMO–LUMO gap, realizing the NIR‐emitting nanographenes.