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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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