On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study
A computational study using density functional theory is reported for selected model aza[n]circulenes (n = 6, 7, 8 and 9) and their derivatives consisting of pyrrole and benzene units. Local aromaticity of central rings was discussed and analyzed using theoretical structural indices. Depending on th...
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| Veröffentlicht in: | Acta Chimica Slovaca 2019-04, Vol.12 (1), p.70-81 |
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| creator | Cagardová, Denisa Lukeš, Vladimír Matúška, Ján Poliak, Peter |
| description | A computational study using density functional theory is reported for selected model aza[n]circulenes (n = 6, 7, 8 and 9) and their derivatives consisting of pyrrole and benzene units. Local aromaticity of central rings was discussed and analyzed using theoretical structural indices. Depending on their molecular structures, energies of the highest occupied and lowest unoccupied molecular orbitals change from –5.23 eV to –4.08 eV and from –1.97 eV to –0.41 eV, respectively. Based on B3LYP calculated optimal geometries, electronic structure of molecules and their charge transport properties resulted in the suggestion of three planar molecules containing three or four pyrrole units as potential candidates for p-type semiconductors. Hole drift mobilities for ideal stacked dimers of these potential semiconductors were calculated and they range from 0.94 cm
2
·V
−1
·s
−1
to 7.33 cm
2
·V
−1
·s
−1
. |
| doi_str_mv | 10.2478/acs-2019-0011 |
| format | Article |
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2
·V
−1
·s
−1
to 7.33 cm
2
·V
−1
·s
−1
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2
·V
−1
·s
−1
to 7.33 cm
2
·V
−1
·s
−1
.</description><subject>Aromaticity</subject><subject>Benzene</subject><subject>Charge transport</subject><subject>Circulenes</subject><subject>Density functional theory</subject><subject>Dimers</subject><subject>Electronic structure</subject><subject>Molecular orbitals</subject><subject>Molecular structure</subject><subject>P-type semiconductors</subject><subject>Semiconductors</subject><subject>Transport properties</subject><issn>1337-978X</issn><issn>1337-978X</issn><issn>1339-3065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNpNkEtLAzEURgdRsNQu3QfcKDQ6eU4iuJD6hEI3CoJISDMJjkyTmmQW9deboS5c3Q_ux-HeU1WnqL7EtBFX2iSIayRhXSN0UE0QIQ2UjXg7_JePq1lK3bqmjCDBKJ1UceVBH4zugY5ho3NnurwDwYFke2uybcEmtLZsfzR89x-mi2borbcJnHtwA_gcNHMggPYtkBfX4M76NALc4E3ugi_c_GlDtAVccspDuzupjpzuk539zWn1-nD_sniCy9Xj8-J2CQ3BOENuEJeWcSoaQ8jaUL42piVCO8YEJpojaR2R2EneGNHq8jtlbU1k47imxpFpdbbnbmP4HmzK6isMsZyUFMaMC8GI5KUF9y0TQ0rROrWN3UbHnUK1Gs2qYlaNZtVolvwC-VVq2Q</recordid><startdate>20190401</startdate><enddate>20190401</enddate><creator>Cagardová, Denisa</creator><creator>Lukeš, Vladimír</creator><creator>Matúška, Ján</creator><creator>Poliak, Peter</creator><general>De Gruyter Poland</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7SR</scope><scope>7U5</scope><scope>7X7</scope><scope>7XB</scope><scope>8AO</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>K9.</scope><scope>KB.</scope><scope>L6V</scope><scope>L7M</scope><scope>M0S</scope><scope>M7S</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope></search><sort><creationdate>20190401</creationdate><title>On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study</title><author>Cagardová, Denisa ; 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Local aromaticity of central rings was discussed and analyzed using theoretical structural indices. Depending on their molecular structures, energies of the highest occupied and lowest unoccupied molecular orbitals change from –5.23 eV to –4.08 eV and from –1.97 eV to –0.41 eV, respectively. Based on B3LYP calculated optimal geometries, electronic structure of molecules and their charge transport properties resulted in the suggestion of three planar molecules containing three or four pyrrole units as potential candidates for p-type semiconductors. Hole drift mobilities for ideal stacked dimers of these potential semiconductors were calculated and they range from 0.94 cm
2
·V
−1
·s
−1
to 7.33 cm
2
·V
−1
·s
−1
.</abstract><cop>Bratislava</cop><pub>De Gruyter Poland</pub><doi>10.2478/acs-2019-0011</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record> |
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| source | Walter De Gruyter: Open Access Journals; EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection |
| subjects | Aromaticity Benzene Charge transport Circulenes Density functional theory Dimers Electronic structure Molecular orbitals Molecular structure P-type semiconductors Semiconductors Transport properties |
| title | On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study |
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