Synthesis and characterization of monolayers and Langmuir - Blodgett Films of an amphiphilic oligo(ethylene glycol)-C6o-hexadecaaniline conjugate

Zhexiong Tang; Prashant A. Padmawar; Taizoon Canteenwala; Yuan Gao; Erik Watkins; Jaroslaw Majewski; Long Y. Chiang; Hsing Lin Wang

doi:10.1021/la060083i

Synthesis and characterization of monolayers and Langmuir - Blodgett Films of an amphiphilic oligo(ethylene glycol)-C_6o-hexadecaaniline conjugate

Zhexiong Tang, Prashant A. Padmawar, Taizoon Canteenwala, Yuan Gao, Erik Watkins, Jaroslaw Majewski, Long Y. Chiang, Hsing Lin Wang

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

A novel amphiphilic oligo(ethylene glycol)-C₆₀ -hexadecaaniline (A₁₆) tricomponent nt conjugate, C₆₀>(A ₁₆-EG₄₃), possessing a well-defined number of repeating aniline donor units and a hydrophilic ethylene glycol oligomer chain was synthesized. The compound is composed of a covalently bound donor-acceptor chromophore structure. Molecular self-assembly of C₆₀>(A ₁₆-EG₄₃) at the air-water interface formed a densely packed Langmuir monolayer with all highly hydrophobic fullerene cages located above the liquid interface. The monolayer can then be transferred onto a glass substrate via Langmuir-Blodgett (LB) deposition. LB multilayered thin films formed by multiple deposition of the monolayer yielded broadened optical absorption peaks extending beyond 600 nm into the 950 nm region, suggesting strong intermolecular interactions among the C₆₀ cages and the A ₁₆ moieties. An X-ray reflectometry study clearly reveals that the Langmuir film at the air-water interface consists of a C₆₀ top layer and a bottom layer containing hexcadecaaniline and oligo(ethylene glycol) with gradually decreasing electron density over a distance of approximately 130 Å above bulk water. The pressure isotherm shows that the packing density of the C_6o>(A₁₆-EG₄₃) monolayer, corresponding to a molecular area of ∼95 Å²/molecule, is similar to that of the surface area of the C₆₀ monolayer. This result suggests that C_6o packing plays a dominant role in guiding the formation of the monolayer structure. Further photoexcitation of hexadecaaniline moieties of aligned (C_6o>)-A₁₆ layers by a flash light source induces cross linking between adjacent A₁₆ segments forming an interlinked A₁₆ array. Our results have demonstrated a unique fabrication method for preparing the aligned donor-acceptor array using strong intermolecular interactions between fullerenes as the molecular orientation guiding force in the Langmuir-Blodgett technique.

Original language	English
Pages (from-to)	5366-5373
Number of pages	8
Journal	Langmuir
Volume	22
Issue number	12
DOIs	https://doi.org/10.1021/la060083i
State	Published - Jun 6 2006
Externally published	Yes

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@article{668fb3485f8e4189b265ec9ed4c73c5b,

title = "Synthesis and characterization of monolayers and Langmuir - Blodgett Films of an amphiphilic oligo(ethylene glycol)-C6o-hexadecaaniline conjugate",

abstract = "A novel amphiphilic oligo(ethylene glycol)-C60 -hexadecaaniline (A16) tricomponent nt conjugate, C60>(A 16-EG43), possessing a well-defined number of repeating aniline donor units and a hydrophilic ethylene glycol oligomer chain was synthesized. The compound is composed of a covalently bound donor-acceptor chromophore structure. Molecular self-assembly of C60>(A 16-EG43) at the air-water interface formed a densely packed Langmuir monolayer with all highly hydrophobic fullerene cages located above the liquid interface. The monolayer can then be transferred onto a glass substrate via Langmuir-Blodgett (LB) deposition. LB multilayered thin films formed by multiple deposition of the monolayer yielded broadened optical absorption peaks extending beyond 600 nm into the 950 nm region, suggesting strong intermolecular interactions among the C60 cages and the A 16 moieties. An X-ray reflectometry study clearly reveals that the Langmuir film at the air-water interface consists of a C60 top layer and a bottom layer containing hexcadecaaniline and oligo(ethylene glycol) with gradually decreasing electron density over a distance of approximately 130 {\AA} above bulk water. The pressure isotherm shows that the packing density of the C6o>(A16-EG43) monolayer, corresponding to a molecular area of ∼95 {\AA}2/molecule, is similar to that of the surface area of the C60 monolayer. This result suggests that C6o packing plays a dominant role in guiding the formation of the monolayer structure. Further photoexcitation of hexadecaaniline moieties of aligned (C6o>)-A16 layers by a flash light source induces cross linking between adjacent A16 segments forming an interlinked A16 array. Our results have demonstrated a unique fabrication method for preparing the aligned donor-acceptor array using strong intermolecular interactions between fullerenes as the molecular orientation guiding force in the Langmuir-Blodgett technique.",

author = "Zhexiong Tang and Padmawar, \{Prashant A.\} and Taizoon Canteenwala and Yuan Gao and Erik Watkins and Jaroslaw Majewski and Chiang, \{Long Y.\} and Wang, \{Hsing Lin\}",

year = "2006",

month = jun,

day = "6",

doi = "10.1021/la060083i",

language = "English",

volume = "22",

pages = "5366--5373",

journal = "Langmuir",

issn = "0743-7463",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Synthesis and characterization of monolayers and Langmuir - Blodgett Films of an amphiphilic oligo(ethylene glycol)-C6o-hexadecaaniline conjugate

AU - Tang, Zhexiong

AU - Padmawar, Prashant A.

AU - Canteenwala, Taizoon

AU - Gao, Yuan

AU - Watkins, Erik

AU - Majewski, Jaroslaw

AU - Chiang, Long Y.

AU - Wang, Hsing Lin

PY - 2006/6/6

Y1 - 2006/6/6

N2 - A novel amphiphilic oligo(ethylene glycol)-C60 -hexadecaaniline (A16) tricomponent nt conjugate, C60>(A 16-EG43), possessing a well-defined number of repeating aniline donor units and a hydrophilic ethylene glycol oligomer chain was synthesized. The compound is composed of a covalently bound donor-acceptor chromophore structure. Molecular self-assembly of C60>(A 16-EG43) at the air-water interface formed a densely packed Langmuir monolayer with all highly hydrophobic fullerene cages located above the liquid interface. The monolayer can then be transferred onto a glass substrate via Langmuir-Blodgett (LB) deposition. LB multilayered thin films formed by multiple deposition of the monolayer yielded broadened optical absorption peaks extending beyond 600 nm into the 950 nm region, suggesting strong intermolecular interactions among the C60 cages and the A 16 moieties. An X-ray reflectometry study clearly reveals that the Langmuir film at the air-water interface consists of a C60 top layer and a bottom layer containing hexcadecaaniline and oligo(ethylene glycol) with gradually decreasing electron density over a distance of approximately 130 Å above bulk water. The pressure isotherm shows that the packing density of the C6o>(A16-EG43) monolayer, corresponding to a molecular area of ∼95 Å2/molecule, is similar to that of the surface area of the C60 monolayer. This result suggests that C6o packing plays a dominant role in guiding the formation of the monolayer structure. Further photoexcitation of hexadecaaniline moieties of aligned (C6o>)-A16 layers by a flash light source induces cross linking between adjacent A16 segments forming an interlinked A16 array. Our results have demonstrated a unique fabrication method for preparing the aligned donor-acceptor array using strong intermolecular interactions between fullerenes as the molecular orientation guiding force in the Langmuir-Blodgett technique.

AB - A novel amphiphilic oligo(ethylene glycol)-C60 -hexadecaaniline (A16) tricomponent nt conjugate, C60>(A 16-EG43), possessing a well-defined number of repeating aniline donor units and a hydrophilic ethylene glycol oligomer chain was synthesized. The compound is composed of a covalently bound donor-acceptor chromophore structure. Molecular self-assembly of C60>(A 16-EG43) at the air-water interface formed a densely packed Langmuir monolayer with all highly hydrophobic fullerene cages located above the liquid interface. The monolayer can then be transferred onto a glass substrate via Langmuir-Blodgett (LB) deposition. LB multilayered thin films formed by multiple deposition of the monolayer yielded broadened optical absorption peaks extending beyond 600 nm into the 950 nm region, suggesting strong intermolecular interactions among the C60 cages and the A 16 moieties. An X-ray reflectometry study clearly reveals that the Langmuir film at the air-water interface consists of a C60 top layer and a bottom layer containing hexcadecaaniline and oligo(ethylene glycol) with gradually decreasing electron density over a distance of approximately 130 Å above bulk water. The pressure isotherm shows that the packing density of the C6o>(A16-EG43) monolayer, corresponding to a molecular area of ∼95 Å2/molecule, is similar to that of the surface area of the C60 monolayer. This result suggests that C6o packing plays a dominant role in guiding the formation of the monolayer structure. Further photoexcitation of hexadecaaniline moieties of aligned (C6o>)-A16 layers by a flash light source induces cross linking between adjacent A16 segments forming an interlinked A16 array. Our results have demonstrated a unique fabrication method for preparing the aligned donor-acceptor array using strong intermolecular interactions between fullerenes as the molecular orientation guiding force in the Langmuir-Blodgett technique.

UR - https://www.scopus.com/pages/publications/33745467304

U2 - 10.1021/la060083i

DO - 10.1021/la060083i

M3 - Article

AN - SCOPUS:33745467304

SN - 0743-7463

VL - 22

SP - 5366

EP - 5373

JO - Langmuir

JF - Langmuir

IS - 12

ER -

Synthesis and characterization of monolayers and Langmuir - Blodgett Films of an amphiphilic oligo(ethylene glycol)-C_6o-hexadecaaniline conjugate

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