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; Juan C Noveron

doi:10.1016/j.bioorg.2014.06.005

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

Bioorg Chem. 2014 Oct:56:62-6. doi: 10.1016/j.bioorg.2014.06.005. Epub 2014 Jul 7.

Authors

Alejandro Bugarin¹, Luis E Martinez², Peter Cooke³, Tadiqul Islam⁴, Juan C Noveron⁴

Affiliations

¹ Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019, USA. Electronic address: bugarin@uta.edu.
² Department of Chemistry and Biochemistry, Trinity University, San Antonio, TX 78212, USA.
³ CURRL, New Mexico State University, 945 College Dr., Las Cruces, NM 88003, USA.
⁴ Department of Chemistry, University of Texas at El Paso, El Paso, TX 79968, USA.

PMID: 25036816
DOI: 10.1016/j.bioorg.2014.06.005

Abstract

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.

Keywords: 1,4-Naphthoquinone; Fischer carbenes; Redox; Solid-phase synthesis; Vesicles.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Micelles
Molecular Structure
Naphthols / chemical synthesis*
Naphthols / chemistry
Naphthoquinones / chemical synthesis*
Naphthoquinones / chemistry
Oxidation-Reduction
Solid-Phase Synthesis Techniques*

Substances

2-tridecanyl-1,4-naphthodiol
2-tridecanyl-1,4-naphthoquinone
Micelles
Naphthols
Naphthoquinones