Multiethynyl Corannulenes: Synthesis, Structure, and Properties.
Syntheses, crystal structures, ab initio density functional theory computations, and photophysical properties of 1,6-di-, 1,2,5,6-tetra-, and 1,3,5,7,9-pentaethynyl-substituted corannulenes (classes 3, 4, and 5, respectively) are reported. Classes 3 and 4 were prepared from the corresponding corannu...
| Publicado en: | Journal of the American Chemical Society Vol. 130; no. 32; pp. 10729 - 10740 |
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| Autores principales: | , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
8/13/2008
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=34064844&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 34064844 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 8/13/2008 vid: 130 iid: 32 pid: 997 pub: American Chemical Society artinfo: ui: 34064844 10.1021/ja802334n ppf: 10729 ppct: 11 formats: tig: atl: Multiethynyl Corannulenes: Synthesis, Structure, and Properties. aug: au: Yao-Ting Wu Bandera, Davide Maag, Roman Linden, Anthony Baldridge, Kim K. Siegel, Jay S. affil: Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland Department of Chemistry, National Cheng-Kung University, No.1 Ta-Hsueh Road, Tainan, Taiwan su: Hydrogen-ion concentration Density functionals Crystals Asymmetric synthesis Chemical reactions sug: subj: Hydrogen-ion concentration Density functionals Crystals Asymmetric synthesis Chemical reactions ab: Syntheses, crystal structures, ab initio density functional theory computations, and photophysical properties of 1,6-di-, 1,2,5,6-tetra-, and 1,3,5,7,9-pentaethynyl-substituted corannulenes (classes 3, 4, and 5, respectively) are reported. Classes 3 and 4 were prepared from the corresponding corannulenyl bromides and terminal alkynes in excellent yields (nine examples, with yields of 57-92%) using the Sonogarshira reaction. Class 5 was prepared from 1,3,5,7,9-pentacholorocorannulene and trimethylalkynylstannanes using a modification of Nolan's procedure (8 examples, with yields of 45-93%). The molecular packing in crystals of 1,6-diphenylethynyl-2,5-dimethylcorannulene (3-Ph) displays a polar columnar structure with all of the molecule bowls oriented in the same direction. Similarly, 1,2,5,6-tetrakis(3,5-dimethylphenylethynyl)corannulene [4-Ar(c)] and 1,3,5,7,9-pentakis(3,5-dimethylphenylethynyl)corannulene [5-Ar(c)] form columnar structures, but the bowls are oriented in opposing directions. Additionally, the number of attached alkynyl arms is correlated with an increase in bowl depth of the corrannulene nucleus. Most of the aryl derivatives displayed high-quantum-efficiency solution luminescence and variable emission wavelengths that were dependent on the nature of the substitution. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2008 holdings: @attributes: islocal: N |
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