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Title: Perforated monolayers: Design and synthesis of porous and cohesive monolayers from mercurated calix(n)arenes

Abstract

Mercuration of a series of O-alkylated calix(n)arenes (produced via reaction of tetrahydroxycalix(4)arene, pentahydroxylcalix(5)arene, hexahydroxycalix(6)arene, and heptahydroxycalix(7)arene with n-bromobutane and with n-bromohexadecane) afford an homologous series of calixarene-based surfactants that form stable monolayers at the air-water interface. Surface pressure-area isotherms, measured for each calixarene, yield limiting areas that are in excellent agreement with values predicted from space-filling models, if it is assumed that the base of each calixarene is parallel and the alkyl chains are perpendicular to the water surface. Introduction of malonic acid to the aqueous subphase results in a substantial increase in the cohesiveness of films derived from calix(4)arene-, calix(5)arene-, and calix(6)arene-based surfactants, as judged by changes in surface viscosity. X-ray photoelectron spectroscopic analysis of a Langmuir-Blodgett film, produced from a malonic acid stabilized calix(6)arene monolayer, shows a carboxylate/mercury ratio of 0.9.

Authors:
; ;  [1];  [2]
  1. Lehigh Univ., Bethlehem, PA (USA)
  2. Univ. of Washington, Seattle (USA)
Publication Date:
OSTI Identifier:
6950058
Resource Type:
Journal Article
Journal Name:
Journal of the American Chemical Society; (USA)
Additional Journal Information:
Journal Volume: 111:21; Journal ID: ISSN 0002-7863
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; MEMBRANE PORES; THIN FILMS; DESIGN; SYNTHESIS; CALCULATION METHODS; DATA ANALYSIS; EXPERIMENTAL DATA; MEASURING INSTRUMENTS; MEASURING METHODS; ORGANIC MERCURY COMPOUNDS; SURFACTANTS; DATA; FILMS; INFORMATION; MERCURY COMPOUNDS; NUMERICAL DATA; ORGANIC COMPOUNDS; 360601* - Other Materials- Preparation & Manufacture; 400200 - Inorganic, Organic, & Physical Chemistry

Citation Formats

Markowitz, M A, Janout, V, Regen, S L, and Castner, D G. Perforated monolayers: Design and synthesis of porous and cohesive monolayers from mercurated calix(n)arenes. United States: N. p., 1989. Web. doi:10.1021/ja00203a020.
Markowitz, M A, Janout, V, Regen, S L, & Castner, D G. Perforated monolayers: Design and synthesis of porous and cohesive monolayers from mercurated calix(n)arenes. United States. doi:10.1021/ja00203a020.
Markowitz, M A, Janout, V, Regen, S L, and Castner, D G. Wed . "Perforated monolayers: Design and synthesis of porous and cohesive monolayers from mercurated calix(n)arenes". United States. doi:10.1021/ja00203a020.
@article{osti_6950058,
title = {Perforated monolayers: Design and synthesis of porous and cohesive monolayers from mercurated calix(n)arenes},
author = {Markowitz, M A and Janout, V and Regen, S L and Castner, D G},
abstractNote = {Mercuration of a series of O-alkylated calix(n)arenes (produced via reaction of tetrahydroxycalix(4)arene, pentahydroxylcalix(5)arene, hexahydroxycalix(6)arene, and heptahydroxycalix(7)arene with n-bromobutane and with n-bromohexadecane) afford an homologous series of calixarene-based surfactants that form stable monolayers at the air-water interface. Surface pressure-area isotherms, measured for each calixarene, yield limiting areas that are in excellent agreement with values predicted from space-filling models, if it is assumed that the base of each calixarene is parallel and the alkyl chains are perpendicular to the water surface. Introduction of malonic acid to the aqueous subphase results in a substantial increase in the cohesiveness of films derived from calix(4)arene-, calix(5)arene-, and calix(6)arene-based surfactants, as judged by changes in surface viscosity. X-ray photoelectron spectroscopic analysis of a Langmuir-Blodgett film, produced from a malonic acid stabilized calix(6)arene monolayer, shows a carboxylate/mercury ratio of 0.9.},
doi = {10.1021/ja00203a020},
journal = {Journal of the American Chemical Society; (USA)},
issn = {0002-7863},
number = ,
volume = 111:21,
place = {United States},
year = {1989},
month = {10}
}