Hexayne Amphiphiles and Bolaamphiphiles.

Bomal E; Croué V; Yeo R; Scopelliti R; Frauenrath H

doi:10.1002/chem.201904890

Back

Journal article

Hexayne Amphiphiles and Bolaamphiphiles.

Bomal E Institute of Materials, Laboratory of Macromolecular and Organic Materials, Ecole Polytechnique Fédérale de Lausanne (EPFL), MXG 135, Station 12, 1015, Lausanne, Switzerland.
Croué V Institute of Materials, Laboratory of Macromolecular and Organic Materials, Ecole Polytechnique Fédérale de Lausanne (EPFL), MXG 135, Station 12, 1015, Lausanne, Switzerland.
Yeo R Institute of Materials, Laboratory of Macromolecular and Organic Materials, Ecole Polytechnique Fédérale de Lausanne (EPFL), MXG 135, Station 12, 1015, Lausanne, Switzerland.
Scopelliti R Institute of Chemical Sciences and Engineering (ISIC), Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015, Lausanne, Switzerland.
Frauenrath H Institute of Materials, Laboratory of Macromolecular and Organic Materials, Ecole Polytechnique Fédérale de Lausanne (EPFL), MXG 135, Station 12, 1015, Lausanne, Switzerland.

2020-02-06

Published in:

Chemistry (Weinheim an der Bergstrasse, Germany). - 2020

English Oligoynes with two or more conjugated carbon-carbon triple bonds are useful precursors for carbon-rich nanomaterials. However, their range of applications has so far been severely limited by the challenging syntheses, particularly in the case of oligoynes with functional groups. Here, we report a universal synthetic approach towards both symmetric and unsymmetric, functionalized hexaynes through the use of a modified Eglinton-Galbraith coupling and a sacrificial building block. We demonstrate the versatility of this approach by preparing hexaynes functionalized with phosphonic acid, carboxylic acid, ammonium, or thiol head groups, which serve as neutral, cationogenic, or anionogenic interfacially active groups. We show that these hexaynes are carbon-rich amphiphiles or bolaamphiphiles that self-assemble at liquid-liquid interfaces, on solid surfaces, as well as in aqueous media.

Language