Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks
| Authors | |
|---|---|
| Year of publication | 2018 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| Citation | |
| Web | https://www.sciencedirect.com/science/article/pii/S0040402018305428?via%3Dihub |
| Doi | http://dx.doi.org/10.1016/j.tet.2018.05.025 |
| Keywords | Macrocycles; Phenanthrene; Donor-acceptor; Solvatochromism; Intramolecular charge transfer; Sonogashira cross-coupling |
| Description | Phenanthrylene-ethynylidene macrocycles combining electron donor and electron acceptor subunits in their shape-persistent fully conjugated core were synthesized. The donor subunits consisted of two 9,10-dialkoxyphenanthrenes linked either with 1,2-ethynylidene or 2,5-thienylene bridge. The acceptors were 9,10-phenanthroquinone and dibenzoquinoxaline and dibenzophenazines derived from it. Solvatochromic photoluminescence from intramolecular-charge-transfer (ICT) excited state was observed mainly in non-polar solvents. In more polar solvents, the excited states favor non-radiative relaxation. DFT calculated HOMO/LUMO energies of the macrocycles correlate well with spectroscopic and electrochemical data. In the series of substituted dibenzophenazine acceptors a good correlation with Hammett substituent constants sigma(-)(p) was found. (C) 2018 Elsevier Ltd. All rights reserved. |
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