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High‐Mobility Self‐Assembling Truxenone‐Based n‐Type Organic Semiconductors
Author(s) -
GómezEsteban Sandra,
BenitoHernandez Angela,
Termine Roberto,
Hennrich Gunther,
Navarrete Juan T. López,
Ruiz Delgado M. Carmen,
Golemme Attilio,
GómezLor Berta
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.201705760
Subject(s) - stacking , intermolecular force , alkyl , electron mobility , intramolecular force , organic semiconductor , materials science , electron , semiconductor , chemical physics , crystallography , chemistry , stereochemistry , optoelectronics , organic chemistry , molecule , physics , quantum mechanics
The synthesis, self‐assembly, and semiconducting properties of a series of disk‐like truxenone derivatives, functionalized with three peripheral long alkyl chains, either directly attached or distanced by linking phenyl or ethynyl groups, are reported. The strategy of distancing the alkyl chains from the central aromatic cores induces in these discotics well‐ordered columnar assemblies and has a favorable effect on their charge‐carrier mobility. Electron mobility values above 1 cm 2 V −1 S −1 were determined for a truxenone functionalized with three peripheral decynyl chains by means of the space charge–limited current technique. DFT calculations help to rationalize the high mobility values found for these new truxenone‐based systems, indicating efficient intermolecular electronic couplings (fostered by a favorable stacking configuration) and moderate intramolecular reorganization energies for electrons in the origin of such high mobilities.