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Synthesis, Crystal Analysis, and Optoelectronic Properties of Diazole‐Functionalized Acenes and Azaacenes
Author(s) -
Pan Huahang,
Song Tingting,
Yin Xiaomeng,
Jin Pengcheng,
Xiao Jinchong
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705657
Subject(s) - heteroatom , conjugated system , electrochemistry , materials science , semiconductor , doping , crystal (programming language) , organic semiconductor , crystal structure , crystallography , nanotechnology , chemistry , optoelectronics , polymer , organic chemistry , computer science , ring (chemistry) , electrode , programming language , composite material
Doping heteroatoms into the skeletons of parent acenes can provide more opportunities to construct novel thermally and photostable organic π‐conjugated semiconductors. Herein, a family of diazole‐decorated acenes ( APyS and APySe ) and azaacenes ( PyP , PyTh , PyPy , PyPh , and PyAP ) have been successfully synthesized through the classical reactions. Single‐crystal X‐ray analyses showed that these as‐formed diazole‐modified derivatives adopted a twisted topology configuration, whereas the azaacenes display reclining‐chair architectures, besides a twisted structure. All these compounds displayed yellow or red light in solution. Moreover, their electrochemical behaviors were also examined. We also found that the azaacenes exhibited a positive spectroscopic response to acid.