SYNTHESIS AND CHARACTERIZATION OF NOVEL 4-CYNANOPHENYLFUNCTIONALIZED N4,N4,N4′,N4′-TERAPHENYLBENZIDINE (TPB) AS HOLE TRANSPORTING MOLECULAR MATERIALS

Year 2017, Volume: 18 Issue: 5, 1000 - 1007, 31.12.2017

Kamuran Gorgun

https://doi.org/10.18038/aubtda.332785

Abstract

In this
study, a new cyanophenyl-functionalized N4,N4,N4′,N4′-tetraphenylbenzidine
(TPB) containing employable hole-transporting components has been synthesized
with Pd-catalyzed Suzuki-Miyaura cross coupling reaction.
N4,N4,N4′,N4′tetrakis-(4′-cynobiphenyl-4-yl)-biphenyl-4,4′-diamine
(TPB-CN)  was well characterized by 1H
NMR, 13C NMR and CHN elemental analysis. The compound TPB-CN exhibited good
thermal stability and luminescence properties. Time Dependent Density
Functional Theory (TDDFT) computation was carried out to investigate the
structural parameters and to understand the photophysical properties of the
novel TPB-CN compound. The experimental and theoretical calculations performed
to calculate absorption maxima in DCM by UV-Vis and TD-B3LYP/6-31g(d,p) were
compared with each other. To identify crystal structure and to determine
optical band gap of TPB-CN compound, its film form, which was coated on the
glass substrate by spin coating, was used. The band gap of TPB-CN compound both
in film and in solution was determined from the optical absorption measurements.

Keywords

N4N4N4′N4′-tetraphenylbenzidine (TPB), Suzuki-Miyaura cross-coupling, Organic semiconductor, TDDFT

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