Long Range Electronic Effects on the Host-Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities

Michal Farber, Pintu Maity, Abhishek Baheti, Adina Golombek, Tal Schwartz, Roman Dobrovetsky*, Arkadi Vigalok*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)15983-15988
Number of pages6
JournalJournal of Organic Chemistry
Volume88
Issue number22
DOIs
StatePublished - 17 Nov 2023

Funding

FundersFunder number
Israel Science Foundation1328/20

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