Please use this identifier to cite or link to this item: https://hdl.handle.net/11147/5393
Title: Donor- and/or acceptor-substituted expanded radialenes: Theory, synthesis, and properties
Authors: Ramsaywack, Sharwatie
Karaca, Sıla
Gholami, Mojtaba
Murray, Adrian H.
Hampel, Frank
McDonald, Robert
Elmacı, Nuran
Lüthi, Hans Peter
Tykwinski, Rik R.
Keywords: Absorption spectroscopy
Ring-closing reactions
Protecting group
Density functional theory
Chemical bonds
Organic polymers
Issue Date: Nov-2014
Publisher: American Chemical Society
Source: Journal of Organic Chemistry, 79(21), 10013-10029. doi:10.1021/jo5016085
Abstract: The synthesis of donor- (D) and/or acceptor (A)-expanded [4]radialenes has been developed on the basis of readily available dibromoolefin (7), tetraethynylethene (10 and 20), and vinyl triflate (12) building blocks. The successful formation of D/A radialenes relies especially on (1) effective use of a series alkynyl protecting groups, (2) Sonogashira cross-coupling reactions, and (3) the development of ring closing reactions to form the desired macrocyclic products. The expanded [4]radialene products have been investigated by spectroscopic (UV-vis absorption and emission) and quantum chemical computational methods (density functional theory and time dependent DFT). The combined use of theory and experiment provides a basis to evaluate the extent of D/A interactions via the cross-conjugated radialene framework as well as an interpretation of the origin of D/A interactions at an orbital level.
URI: https://doi.org/10.1021/jo5016085
http://hdl.handle.net/11147/5393
ISSN: 0022-3263
Appears in Collections:Chemistry / Kimya
PubMed İndeksli Yayınlar Koleksiyonu / PubMed Indexed Publications Collection
Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection

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