Premium
Hexayne Amphiphiles and Bolaamphiphiles
Author(s) -
Bomal Enzo,
Croué Vincent,
Yeo Reuben,
Scopelliti Rosario,
Frauenrath Holger
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904890
Subject(s) - amphiphile , conjugated system , carbon fibers , aqueous solution , materials science , thiol , combinatorial chemistry , nanotechnology , chemistry , organic chemistry , polymer chemistry , composite number , copolymer , polymer , composite material
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.