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Synthesis and Electronic Properties of Triperyleno[3.3.3]Propellanes: Towards Two‐Dimensional Electronic Structures
Author(s) -
Kodama Takuya,
Miyazaki Shogo,
Kubo Takashi
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201800614
Subject(s) - perylene , delocalized electron , bathochromic shift , chemistry , molecule , absorption spectroscopy , photochemistry , absorption (acoustics) , electron delocalization , electronic structure , crystallography , computational chemistry , materials science , organic chemistry , physics , fluorescence , quantum mechanics , composite material
Threefold symmetric triperyleno[3.3.3]propellanes (TPRPs), which are composed of three perylene units peri ‐fused on [3.3.3]proppellane, have been synthesized and their electronic properties characterized. Unsubstituted TPRP assembles into two‐dimensional honeycomb‐like networks. TPRP displays a bathochromic‐shifted absorption band in its absorption spectrum and shows well‐separated one‐electron redox waves in a cyclic voltammogram, due to a homoconjugative interaction between perylene moieties. A radical cation species of tert ‐butyl substituted TPRP shows spin delocalization over the whole of the molecule, which is derived from effective overlap of HOMOs among three perylene moieties.