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Title: Self-assembly of aromatic-derivatized amphiphiles: Phenyl, biphenyl, and terphenyl fatty acids and phospholipids

Abstract

This paper reports the synthesis of a series of amphiphiles (fatty acids and phosphatidylcholine derivatives) containing phenyl, biphenyl, and terphenyl chromophores inserted in the hydrocarbon chain and a study of their self-assembly in Langmuir-Blodgett films and aqueous dispersions. As observed and reported earlier for amphiphiles containing trans-stilbene, styrylthiophene, or azobenzene chromophores, several of the biphenyl and terphenyl derivatives show strong evidence of ground state association to form H aggregates characterized by a blue shift in absorption and a structured, red-shifted fluorescence. The phenyl amphiphiles show different behavior, suggesting that, even for pure films or bilayers, there is very little or no ground state association. For the biphenyl and terphenyl phospholipids, aqueous suspensions obtained by sonication are closed bilayer vesicles similar in size to those formed from the corresponding saturated phospholipids. The overall results of the present study indicate that biphenyl and terphenyl amphiphiles undergo aggregation processes to form compact arrays formally similar to those observed with stilbenen tolan, azobenzene, and squaraine derivatives but that the aromatic-aromatic interactions are considerably weaker than those for the more extended aromatics and lead to less distortion of the assembly structure.

Authors:
; ; ; ;  [1]
  1. Univ. of Rochester, NY (United States)|[Los Alamos National Lab., NM (United States). Chemical Science and Technology Div.
Publication Date:
Sponsoring Org.:
USDOE, Washington, DC (United States)
OSTI Identifier:
696638
Resource Type:
Journal Article
Journal Name:
Langmuir
Additional Journal Information:
Journal Volume: 15; Journal Issue: 17; Other Information: PBD: 17 Aug 1999
Country of Publication:
United States
Language:
English
Subject:
40 CHEMISTRY; FILMS; PHOSPHOLIPIDS; CARBOXYLIC ACIDS; DISPERSIONS; SUSPENSIONS

Citation Formats

Geiger, H.C., Perlstein, J., Lachicotte, R.J., Wyrozebski, K., and Whitten, D.G. Self-assembly of aromatic-derivatized amphiphiles: Phenyl, biphenyl, and terphenyl fatty acids and phospholipids. United States: N. p., 1999. Web. doi:10.1021/la990124t.
Geiger, H.C., Perlstein, J., Lachicotte, R.J., Wyrozebski, K., & Whitten, D.G. Self-assembly of aromatic-derivatized amphiphiles: Phenyl, biphenyl, and terphenyl fatty acids and phospholipids. United States. doi:10.1021/la990124t.
Geiger, H.C., Perlstein, J., Lachicotte, R.J., Wyrozebski, K., and Whitten, D.G. Tue . "Self-assembly of aromatic-derivatized amphiphiles: Phenyl, biphenyl, and terphenyl fatty acids and phospholipids". United States. doi:10.1021/la990124t.
@article{osti_696638,
title = {Self-assembly of aromatic-derivatized amphiphiles: Phenyl, biphenyl, and terphenyl fatty acids and phospholipids},
author = {Geiger, H.C. and Perlstein, J. and Lachicotte, R.J. and Wyrozebski, K. and Whitten, D.G.},
abstractNote = {This paper reports the synthesis of a series of amphiphiles (fatty acids and phosphatidylcholine derivatives) containing phenyl, biphenyl, and terphenyl chromophores inserted in the hydrocarbon chain and a study of their self-assembly in Langmuir-Blodgett films and aqueous dispersions. As observed and reported earlier for amphiphiles containing trans-stilbene, styrylthiophene, or azobenzene chromophores, several of the biphenyl and terphenyl derivatives show strong evidence of ground state association to form H aggregates characterized by a blue shift in absorption and a structured, red-shifted fluorescence. The phenyl amphiphiles show different behavior, suggesting that, even for pure films or bilayers, there is very little or no ground state association. For the biphenyl and terphenyl phospholipids, aqueous suspensions obtained by sonication are closed bilayer vesicles similar in size to those formed from the corresponding saturated phospholipids. The overall results of the present study indicate that biphenyl and terphenyl amphiphiles undergo aggregation processes to form compact arrays formally similar to those observed with stilbenen tolan, azobenzene, and squaraine derivatives but that the aromatic-aromatic interactions are considerably weaker than those for the more extended aromatics and lead to less distortion of the assembly structure.},
doi = {10.1021/la990124t},
journal = {Langmuir},
number = 17,
volume = 15,
place = {United States},
year = {1999},
month = {8}
}