jp6b09888_si_001.pdf (798.85 kB)
Halogen Substitution Effects on the Molecular Packing and Thin Film Transistor Performances of Carbazoledioxazine Derivatives
journal contribution
posted on 2016-11-08, 00:00 authored by Hiroki Tatsumi, Yang Wang, Yosuke Aizawa, Masatoshi Tokita, Takehiko Mori, Tsuyoshi MichinobuSolution-processable
carbazoledioxazine derivatives with different
halogen substituents (F, Cl, and Br) were newly synthesized by condensation
and subsequent cyclization reactions. The chemical structures were
confirmed by 1H NMR and IR spectroscopies as well as MALDI-TOF
mass spectrometry. All three carbazoledioxazines possessed a high
thermal stability with decomposition temperatures exceeding 270 °C
and exhibited thermal transitions upon heating. The phases were characterized
by their wide-angle X-ray diffraction patterns at various temperatures.
In addition, the energy levels of the carbazoledioxazines were estimated
from the optical absorption spectra and electrochemical redox potentials
of the thin films. All three derivatives displayed more or less the
same energy levels: highest occupied molecular orbitals (HOMOs) of
−5.3 eV and lowest unoccupied molecular orbitals (LUMOs) of
−3.5 ∼ −3.6 eV. Despite this fact, the Br derivative
showed higher hole mobilities with the maximum mobility of 4.9 ×
10–3 cm2 V–1 s–1 in the thin film transistors as compared to those
of the counter F and Cl derivatives. This was attributed to the bimodal
carrier pathways formed through the monoclinic molecular orientation
of the Br derivative, revealed by grazing-incidence X-ray diffraction
(GIXRD) measurements.
History
Usage metrics
Categories
Keywords
wide-angle X-ray diffraction patternsBrelectrochemical redox potentialsLUMO1 H NMReVGIXRDThin Film Transistor PerformancesHalogen Substitution EffectsHOMOgrazing-incidence X-ray diffractionCarbazoledioxazine Derivatives Solution-processable carbazoledioxazine derivativesClfilmorbitalMALDI-TOF mass spectrometryIRenergy levelsbimodal carrier pathways
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC