Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene

Handle URI:
http://hdl.handle.net/10754/623136
Title:
Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene
Authors:
Shi, Xueliang; Kueh, Weixiang; Zheng, Bin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Chi, Chunyan
Abstract:
Quinoidal thia-acene analogues, as the respective isoelectronic structures of pentacene and nonacene, were synthesized and an unusual 1,2-sulfur migration was observed during the Friedel-Crafts alkylation reaction. The analogues display a closed-shell quinoidal structure in the ground state with a distinctive dipolar character. In contrast to their acene isoelectronic structures, both compounds are stable because of the existence of more aromatic sextet rings, a dipolar character, and kinetic blocking. They exhibit unique packing in single crystals resulting from balanced dipole-dipole and [C-H⋯π]/[C-H⋯S] interactions.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division
Citation:
Shi X, Kueh W, Zheng B, Huang K-W, Chi C (2015) Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene. Angewandte Chemie International Edition 54: 14412–14416. Available: http://dx.doi.org/10.1002/anie.201507573.
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
8-Oct-2015
DOI:
10.1002/anie.201507573; 10.1002/ange.201507573
PubMed ID:
26447720
Type:
Article
ISSN:
1433-7851
Sponsors:
C.C. acknowledges financial support from the MOE Tier 1 grant (R-143-000-573-112), Tier 2 grant (MOE2014-T2-1-080), and Tier 3 programme (MOE2014-T3-1-004). K.-W.H. acknowledges financial support from KAUST. We thank Dr. Bruno Donnadieu and Dr. Tan Geok Kheng for the crystallographic analysis.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorShi, Xueliangen
dc.contributor.authorKueh, Weixiangen
dc.contributor.authorZheng, Binen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorChi, Chunyanen
dc.date.accessioned2017-04-13T11:50:56Z-
dc.date.available2017-04-13T11:50:56Z-
dc.date.issued2015-10-08en
dc.identifier.citationShi X, Kueh W, Zheng B, Huang K-W, Chi C (2015) Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene. Angewandte Chemie International Edition 54: 14412–14416. Available: http://dx.doi.org/10.1002/anie.201507573.en
dc.identifier.issn1433-7851en
dc.identifier.pmid26447720en
dc.identifier.doi10.1002/anie.201507573en
dc.identifier.doi10.1002/ange.201507573en
dc.identifier.urihttp://hdl.handle.net/10754/623136-
dc.description.abstractQuinoidal thia-acene analogues, as the respective isoelectronic structures of pentacene and nonacene, were synthesized and an unusual 1,2-sulfur migration was observed during the Friedel-Crafts alkylation reaction. The analogues display a closed-shell quinoidal structure in the ground state with a distinctive dipolar character. In contrast to their acene isoelectronic structures, both compounds are stable because of the existence of more aromatic sextet rings, a dipolar character, and kinetic blocking. They exhibit unique packing in single crystals resulting from balanced dipole-dipole and [C-H⋯π]/[C-H⋯S] interactions.en
dc.description.sponsorshipC.C. acknowledges financial support from the MOE Tier 1 grant (R-143-000-573-112), Tier 2 grant (MOE2014-T2-1-080), and Tier 3 programme (MOE2014-T3-1-004). K.-W.H. acknowledges financial support from KAUST. We thank Dr. Bruno Donnadieu and Dr. Tan Geok Kheng for the crystallographic analysis.en
dc.publisherWiley-Blackwellen
dc.subjectaromaticityen
dc.subjectdensity functional calculationsen
dc.subjectpolycyclic aromatic hydrocarbonsen
dc.subjectstructure determinationen
dc.subjectX-ray diffractionen
dc.titleDipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonaceneen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, Singaporeen
kaust.authorZheng, Binen
kaust.authorHuang, Kuo-Weien

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