jo402365s_si_004.cif (1.3 MB)
Diindole-Annulated Naphthalene Diimides: Synthesis and Optical and Electronic Properties of Syn- and Anti-Isomers
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posted on 2014-01-03, 00:00 authored by Sabin-Lucian Suraru, Christian Burschka, Frank WürthnerHere
we report a selective method for the core-extension of naphthalene
diimide (NDI) with two annulated indole rings leading to carbazolo[2,3-b]carbazole diimides (CbDIs) with exclusive syn-connectivity based on a regioselective nucleophilic substitution
reaction of Br4-NDI with arylamines, followed by palladium-catalyzed
intramolecular C–C coupling. The oxygen analogues of anti-CbDIs, namely anti-benzofurobenzofuran
diimides (anti-BfDIs), were obtained from 2,6-Br2-NDI and 2-bromophenol. The syn- and anti-isomers of CbDIs were unambiguously characterized by
single-crystal X-ray analysis. The optical properties of the present
core-enlarged NDIs were studied, revealing clear differences in the
absorption characteristics of the syn- and anti-isomers of CbDI, on one hand, and CbDI vs BfDI derivatives,
on the other hand. Cyclic voltammetry studies showed that the redox
properties are dependent on the substituents at the CbDI-core and
oxygen atom containing BfDIs are more prone to reduction than the
respective nitrogen analogues CbDIs. Vacuum-processed organic field
effect transistors reveal CbDI and BfDI derivatives with n-channel,
p-channel, as well as ambient transport characteristics with mobility
values up to 0.2 cm2/(V s).
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ambient transport characteristicsredox propertiesabsorption characteristicsnaphthalene diimideElectronic Propertiesnitrogen analogues CbDIsBfDI derivativesNDIannulated indole ringsmobility valuesfield effect transistorsCbDI vs BfDI derivativesoxygen atomregioselective nucleophilic substitution reactionCyclic voltammetry studiesoxygen analogues
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