Supramolecular Host-Guest Interactions of a Thio-Cyclophane Trimer with Special Emphasis on C₆₀ Binding

Biswas, Shayak (2022) Supramolecular Host-Guest Interactions of a Thio-Cyclophane Trimer with Special Emphasis on C₆₀ Binding. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Shayak Biswas (17MS163)) 17MS163_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (931kB)

Abstract

Supramolecular chemistry involves the binding of a molecule (host) with another molecule (guest) through non-covalent interactions to produce a host-guest species. In this work, we try to characterize a previously unreported molecule- a thiocyclophane trimer. It was obtained as a side production in an intermediate reaction of dihydropyrene (DHP) synthesis. We are trying to characterize it and investigate its ability to function as a supramolecular host; to work as a detector or as a vessel for reactions. The molecule has three disulphide linkages and three nitrile functional groups, making the π rings electron deficient and at the same time the sulphur atoms can act as donor centers. The thiocyclophane trimer shows promising binding capability with BINOL at 1:2 trimer/BINOL concentration (10μM trimer + 20μM BINOL in CHCl₃). There is no conclusive evidence of binding of thiocyclophane trimer with Ag Nanoparticles. The thiocyclophane trimer also shows partial stabilization of C60 molecules as observed from the Cyclic Voltammetry data. Further studies can be conducted to check the viability of the thiocyclophane trimer as a suitable supramolecular host. Binding studies can be conducted with Bisphenol-A, a teratogen which is an agent or factor which causes malformation of an embryo. The thiocyclophane trimer may also be doped with NIR-emitting nanoparticles, which have many medical implications, and its efficacy as a catalyst/reaction vesicle may be studied. The -CN functionalities of the thiocyclophane trimer may be oxidized to -COOH functionalities, which would open up possibilities for the trimer to act as supramolecular host for a wide new range of electron-deficient species.

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