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α‐Iminonitriles: Composite Functional Groups for Functionalization of Pyrene
Author(s) -
Deng Guigang,
Liu Tianqi,
Wang Yuqin,
Liu Bingxin,
Tan Qitao,
Xu Bin
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000585
Subject(s) - chemistry , surface modification , pyrene , stacking , imine , functional group , combinatorial chemistry , photochemistry , density functional theory , dibenzothiophene , organic chemistry , polymer , computational chemistry , catalysis
Abstract Functionalization of polycyclic aromatic hydrocarbons (PAHs) with functional groups is essential for tuning the optoelectronic properties, solid stacking and solubility. α‐Iminonitriles are composite functional groups (CFGs) containing imine (C=N−R) and nitrile (CN) moieties with strong electron‐withdrawing character and good stability, which could be readily introduced through several effective synthetic methods. α‐Iminonitriles have been widely used as intermediates for organic transformations but hold untapped potential for modification of organic functional materials. We herein disclose that α‐iminonitriles are eminent groups for modifying the properties of pyrene. The introduction of α‐iminonitriles to pyrene causes many changes: significantly lowering the LUMOs, red‐shift in absorption and emission spectra, tuning the solid‐stacking, triggering aggregation‐induced emission and white‐light emission. This work indicates that CFGs such as α‐iminonitriles may provide extra toolkits for the functionalization of organic functional materials which would help to tap the potentials of novel or existed materials.