Antiaromaticity gain increases the potential for n-type charge transport in hydrogen-bonded π-conjugated cores

Density functional theory computations suggest that formally non-aromatic organic dyes, like diketopyrrolopyrrole, naphthodipyrrolidone, indigo, and isoindigo, show increased [4 n ] π-antiaromatic character and decreased LUMO orbital energies upon hydrogen bonding, making them suitable molecular can...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 13; pp. 28 - 211
Main Authors Wen, Zhili, Wu, Judy I-Chia
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 13.02.2020
Subjects
Charge transport
Density functional theory
Field effect transistors
Hydrogen bonding
Indigo
Molecular orbitals
Semiconductor devices
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Summary:Density functional theory computations suggest that formally non-aromatic organic dyes, like diketopyrrolopyrrole, naphthodipyrrolidone, indigo, and isoindigo, show increased [4 n ] π-antiaromatic character and decreased LUMO orbital energies upon hydrogen bonding, making them suitable molecular candidates for applications in n-type organic field effect transistors. Hydrogen bonding increases antiaromaticity and lowers the LUMO energy levels of non-aromatic π-conjugated cores.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/c9cc09670a
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc09670a