Synthesis and properties of π-conjugated donor–acceptor macrocycles derived from phenanthrylene building blocks
| Autor: | Ctibor Mazal, Sushil Kumar Mishra, Bhimrao Vaijnath Phulwale |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Photoluminescence 010405 organic chemistry Organic Chemistry Solvatochromism Substituent Electron donor Electron acceptor Conjugated system 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Crystallography chemistry.chemical_compound chemistry Excited state Drug Discovery HOMO/LUMO |
| Zdroj: | Tetrahedron. 74:3616-3623 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.05.025 |
| Popis: | 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 σp– was found. |
| Databáze: | OpenAIRE |
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