Preparation, Electronic and Liquid Crystalline Properties of Electron-Accepting Azaacene Derivatives
Author(s) -
Takashi Takeda,
Tomohiro Ikemoto,
S. Yamamoto,
Wakana Matsuda,
Shu Seki,
Masaya Mitsuishi,
Tomoyuki Akutagawa
Publication year - 2018
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.8b01943
Subject(s) - intermolecular force , van der waals force , hydrogen bond , phase (matter) , chemical physics , dipole , intermolecular interaction , electron , materials science , electrochemistry , chemistry , crystallography , molecule , organic chemistry , physics , electrode , quantum mechanics
A series of electron-accepting azaacene-type materials 1 - 4 with different kinds and degrees of intermolecular interactions were synthesized. Simple modification of the terminal substituents significantly modulated the photophysical and electrochemical properties. The degree of weak intermolecular interaction determined the emergence of a liquid crystalline (LC) phase for each compound. Dipole-dipole interaction, π-π interaction, and van der Waals interaction all contributed to stabilize the LC phase of 1 and 2 . The introduction of strong hydrogen bonding interaction enabled the formation of a highly ordered LC phase in 4 . Charge-transport properties of 1 , 2 , and 4 were also investigated.
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