Fluorophobic Effect in the Self-Assembly of Polymers and Model Compounds Containing Tapered Groups into Supramolecular Columns

TLDR: The synthesis and characterization of the tapered building blocks 3,4,5-tris(1H, 1H,2H, 2H,3H, 3H,4H, 4H,5H, 5H,6H, 6H,7H,8H, 8H-perfluorodododecan-1-yloxy)benzoic acid and methacrylates are described.

Abstract: The synthesis and characterization of the tapered building blocks 3,4,5-tris(1H,1H,2H,2H,3H,3H,4H,4H,5H,5H,6H,6H,7H,7H,8H,8H-perfluorododecan-1-yloxy)benzoic acid (11-8/4), 3,4,5-tris(1H,1H,2H,2H,3H,3H,4H,4H,5H,5H,6H,6H-perfluorododecan-1-yloxy)benzoic acid (11-6/6), 3,4,5-tris(1H,1H,2H,2H,3H,3H,4H,4H-perfluorododecan-1-yloxy)benzoic acid (11-4/8), 2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl 3,4,5-tris(1H,1H,2H,2H,3H,3H,4H,4H,5H,5H,6H,6H,7H,7H,8H,8H-perfluorododecan-1-yloxy)benzoate (19-8/4), 2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl 3,4,5-tris(1H,1H,2H,2H,3H,3H,4H,4H,5H,5H,6H,6H-perfluorododecan-1-yloxy)benzoate (19-6/6), and 2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl 3,4,5-tris(1H,1H,2H,2H,3H,3H,4H,4H-perfluorododecan-1-yloxy)benzoate (19-4/8) and of the methacrylates and polymethacrylates of 19-8/4, 19-6/6, and 19-4/8 (i.e, 20-8/4, 20-6/6, 20-4/8 and respectively 21-8/4, 21-6/6, and 21-4/8) are described. All tapered building blocks 11-m/n, 19-m/n, and the polymers 21-m/n (where m + n = 12 and m ...