Pandit, Younis Ahmad ; Sanfui, Sarnali ; Rath, Sankar Prasad (2017) Intermacrocyclic Interaction Triggers Facile One-Pot Synthesis of a Chlorin-Porphyrin Heterodimer Chemistry - A European Journal, 23 (54). pp. 13415-13422. ISSN 0947-6539
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Official URL: http://doi.org/10.1002/chem.201701943
Related URL: http://dx.doi.org/10.1002/chem.201701943
Abstract
This work reports a highly facile one-pot synthesis of a new series of fully π-conjugated unsymmetric chlorin–porphyrin heterodimers with quantitative yields by utilizing intermacrocyclic interactions. One-electron oxidations of dicopper(II) and dipalladium(II) porphyrin dimers using mild oxidants such as iodine at room temperature resulted in the formation of a strongly interacting cofacial mixed-valent π-cation radical dimers. The radical, being highly reactive, drives spontaneous and rapid transformation involving a new N=C bond formation, 1,2-ethyl migration, and the generation of a new indolizinium ring that bridges between the two macrocycles. X-ray structural characterization of the heterodimers reveals that the two macrocycles are nearly coplanar and thereby extends the π-conjugation from one end to the other. DFT calculations that reproduce the experimental results are also reported.
Item Type: | Article |
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Source: | Copyright of this article belongs to John Wiley and Sons, Inc. |
ID Code: | 120838 |
Deposited On: | 06 Jul 2021 06:24 |
Last Modified: | 06 Jul 2021 06:24 |
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