TY - JOUR
T1 - Long Range Electronic Effects on the Host-Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities
AU - Farber, Michal
AU - Maity, Pintu
AU - Baheti, Abhishek
AU - Golombek, Adina
AU - Schwartz, Tal
AU - Dobrovetsky, Roman
AU - Vigalok, Arkadi
N1 - Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.
PY - 2023/11/17
Y1 - 2023/11/17
N2 - We report the synthesis of a series of the oxygen-depleted conjugated 5,5′-Bicalix[4]arene compounds bearing various substituents at the terminal positions of the conjugated chain and their fluorescence response to the presence of a cationic N-methylpyridinium guest. The complexation of this cation within the bicalixarene cavity results in the fluorescence quenching, with the host molecules bearing electron-donating groups demonstrating a stronger fluorescence response. These results show the importance of the electronic effects on the host-guest complexation within the hydrophobic calixarene scaffolds.
AB - We report the synthesis of a series of the oxygen-depleted conjugated 5,5′-Bicalix[4]arene compounds bearing various substituents at the terminal positions of the conjugated chain and their fluorescence response to the presence of a cationic N-methylpyridinium guest. The complexation of this cation within the bicalixarene cavity results in the fluorescence quenching, with the host molecules bearing electron-donating groups demonstrating a stronger fluorescence response. These results show the importance of the electronic effects on the host-guest complexation within the hydrophobic calixarene scaffolds.
UR - http://www.scopus.com/inward/record.url?scp=85178247805&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c01566
DO - 10.1021/acs.joc.3c01566
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C2 - 37906127
AN - SCOPUS:85178247805
SN - 0022-3263
VL - 88
SP - 15983
EP - 15988
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 22
ER -