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Solid-phase organic synthesis of 2-tridecanyl-1,4-naphthoquinone and 2-tridecanyl-1,4-naphthodiol that form redox-active micelles and vesicles
Journal article   Peer reviewed

Solid-phase organic synthesis of 2-tridecanyl-1,4-naphthoquinone and 2-tridecanyl-1,4-naphthodiol that form redox-active micelles and vesicles

Alejandro Bugarin, Luis E Martinez, Peter Cooke, Tadiqul Islam and Juan C Noveron
Bioorganic chemistry, Vol.56, pp.62-66
10-2014
PMID: 25036816

Abstract

1,4-Naphthoquinone Fischer carbenes Redox Solid-phase synthesis Vesicles
•We report high purity adducts by using solid supported Fischer carbenes complexes.•Microwave-assisted Dötz benzannulation was key for the completion of the synthesis.•This new approach allows the easy access to amphiphilic molecules.•The new molecules presented a remarkable quasi-reversible redox potential.•These naphthoquinone derivatives self-assemble into micelles or vesicles. The solid-phase synthesis of new amphiphilic compounds is reported. It is based on a newly designed 1,4-naphthoquinone derivative that contains polar and nonpolar groups and self-assembles into micelles or vesicles in water depending on the concentration. They also display redox-active properties.

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