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@article{1457977,
author = {Phulwale, Bhimrao Vaijnath and Mishra, Sushil Kumar and Mazal, Ctibor},
article_location = {Oxford},
article_number = {27},
doi = {http://dx.doi.org/10.1016/j.tet.2018.05.025},
keywords = {Macrocycles; Phenanthrene; Donor-acceptor; Solvatochromism; Intramolecular charge transfer; Sonogashira cross-coupling},
language = {eng},
issn = {0040-4020},
journal = {Tetrahedron},
title = {Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks},
url = {https://www.sciencedirect.com/science/article/pii/S0040402018305428?via%3Dihub},
volume = {74},
year = {2018}
}
TY - JOUR
ID - 1457977
AU - Phulwale, Bhimrao Vaijnath - Mishra, Sushil Kumar - Mazal, Ctibor
PY - 2018
TI - Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks
JF - Tetrahedron
VL - 74
IS - 27
SP - 3616-3623
EP - 3616-3623
PB - ERGAMON-ELSEVIER SCIENCE LTD
SN - 00404020
KW - Macrocycles
KW - Phenanthrene
KW - Donor-acceptor
KW - Solvatochromism
KW - Intramolecular charge transfer
KW - Sonogashira cross-coupling
UR - https://www.sciencedirect.com/science/article/pii/S0040402018305428?via%3Dihub
N2 - 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.
ER -
PHULWALE, Bhimrao Vaijnath, Sushil Kumar MISHRA and Ctibor MAZAL. Synthesis and properties of pi-conjugated donor-acceptor macrocycles derived from phenanthrylene building blocks. \textit{Tetrahedron}. Oxford: ERGAMON-ELSEVIER SCIENCE LTD, 2018, vol.~74, No~27, p.~3616-3623. ISSN~0040-4020. Available from: https://dx.doi.org/10.1016/j.tet.2018.05.025.
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