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Derivatizing Tribenzothiophene‐Fused Hexa‐ peri ‐hexabenzocoronenes with Tunable Optoelectronic Properties
Author(s) -
Liu Yi,
Marszalek Tomasz,
Müllen Klaus,
Pisula Wojciech,
Feng Xinliang
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600753
Subject(s) - homo/lumo , thiophene , hexa , moiety , cyclic voltammetry , molecular orbital , chemistry , absorption spectroscopy , alkoxy group , crystallography , materials science , photochemistry , stereochemistry , molecule , electrochemistry , organic chemistry , electrode , physics , optics , alkyl
A series of trisbenzothieno[1,2:7,8:13,14]hexa‐ peri ‐hexabenzocoronenes were synthesized and characterized by a combination of NMR, 2D NMR, MALDI‐TOF MS, UV/Vis absorption spectroscopy, and 2D‐WAXS measurement. By structural modulation like decoration of electro‐donating alkoxyl chain, and conversion from an electron‐rich thiophene ring into an electron‐poor thiophene‐ S,S ‐dioxide moiety, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels of the hexabenzocoronenes derivatives can be effectively tuned which is further verified by the DFT calculations and cyclic voltammetry.