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Title: Strategies for Electrooptic Film Fabrication. Influence of Pyrrole-Pyridine-Based Dibranched Chromophore Architecture on Covalent Self-Assembly, Thin-Film Microstructure, and Nonlinear Optical Response

Abstract

The new dibranched, heterocyclic 'push-pull' chromophores bis{l_brace}1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}methane (1), 1-(pyrid-4-yl)-2-(N-methyl-5-formylpyrrol-2-yl)ethylene (2), {l_brace}1-(N-methylpyridinium-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}{l_brace}[1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane]{r_brace}methane (3), N-methyl-2-[1-(N-methylpyrid-4-yl)ethen-2-yl]-5-[pyrid-4-yl]ethen-2-yl-pyrrole iodide (4), bis{l_brace}1-(N-methyl-4-pyridinio)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}methane iodide (5), and N-methyl-2,5-[1-(N-methylpyrid-4-yl)ethen-2-yl]pyrrole iodide (6) have been synthesized and characterized. The neutral (1 and 2) and monomethyl salts (3 and 4) undergo chemisorptive reaction with iodobenzyl-functionalized surfaces to afford chromophore monolayers SA-1/SA-2 and SA-3/SA-4, respectively. Molecular structures and other physicochemical properties have been defined by 1H NMR, optical spectroscopy, and XRD. Thin-film characterization by a variety of techniques (optical spectroscopy, specular X-ray reflectivity, atomic force microscopy, X-ray photoelectron spectroscopy, and angle-dependent polarized second harmonic generation) underscore the importance of the chromophore molecular architecture as well as film growth method on film microstructure and optical/electrooptic response.

Authors:
; ; ; ; ; ; ;
Publication Date:
Research Org.:
Brookhaven National Laboratory (BNL) National Synchrotron Light Source
Sponsoring Org.:
Doe - Office Of Science
OSTI Identifier:
914247
Report Number(s):
BNL-78815-2007-JA
Journal ID: ISSN 0002-7863; JACSAT; TRN: US200809%%10
DOE Contract Number:  
DE-AC02-98CH10886
Resource Type:
Journal Article
Resource Relation:
Journal Name: J. Am. Chem. Soc.; Journal Volume: 128
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; PYRROLES; PYRIDINES; THIN FILMS; FABRICATION; MICROSTRUCTURE; MOLECULAR STRUCTURE; OPTICAL PROPERTIES; ELECTRO-OPTICAL EFFECTS; PHYSICAL PROPERTIES; CHEMICAL PROPERTIES; national synchrotron light source

Citation Formats

Facchetti,A., Beverina, L., van der Boom, M., Shukla, A., Dutta, P., Evmenenko, G., Marks, T., and Pagani, G. Strategies for Electrooptic Film Fabrication. Influence of Pyrrole-Pyridine-Based Dibranched Chromophore Architecture on Covalent Self-Assembly, Thin-Film Microstructure, and Nonlinear Optical Response. United States: N. p., 2006. Web. doi:10.1021/ja057556c.
Facchetti,A., Beverina, L., van der Boom, M., Shukla, A., Dutta, P., Evmenenko, G., Marks, T., & Pagani, G. Strategies for Electrooptic Film Fabrication. Influence of Pyrrole-Pyridine-Based Dibranched Chromophore Architecture on Covalent Self-Assembly, Thin-Film Microstructure, and Nonlinear Optical Response. United States. doi:10.1021/ja057556c.
Facchetti,A., Beverina, L., van der Boom, M., Shukla, A., Dutta, P., Evmenenko, G., Marks, T., and Pagani, G. Sun . "Strategies for Electrooptic Film Fabrication. Influence of Pyrrole-Pyridine-Based Dibranched Chromophore Architecture on Covalent Self-Assembly, Thin-Film Microstructure, and Nonlinear Optical Response". United States. doi:10.1021/ja057556c.
@article{osti_914247,
title = {Strategies for Electrooptic Film Fabrication. Influence of Pyrrole-Pyridine-Based Dibranched Chromophore Architecture on Covalent Self-Assembly, Thin-Film Microstructure, and Nonlinear Optical Response},
author = {Facchetti,A. and Beverina, L. and van der Boom, M. and Shukla, A. and Dutta, P. and Evmenenko, G. and Marks, T. and Pagani, G.},
abstractNote = {The new dibranched, heterocyclic 'push-pull' chromophores bis{l_brace}1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}methane (1), 1-(pyrid-4-yl)-2-(N-methyl-5-formylpyrrol-2-yl)ethylene (2), {l_brace}1-(N-methylpyridinium-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}{l_brace}[1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane]{r_brace}methane (3), N-methyl-2-[1-(N-methylpyrid-4-yl)ethen-2-yl]-5-[pyrid-4-yl]ethen-2-yl-pyrrole iodide (4), bis{l_brace}1-(N-methyl-4-pyridinio)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}methane iodide (5), and N-methyl-2,5-[1-(N-methylpyrid-4-yl)ethen-2-yl]pyrrole iodide (6) have been synthesized and characterized. The neutral (1 and 2) and monomethyl salts (3 and 4) undergo chemisorptive reaction with iodobenzyl-functionalized surfaces to afford chromophore monolayers SA-1/SA-2 and SA-3/SA-4, respectively. Molecular structures and other physicochemical properties have been defined by 1H NMR, optical spectroscopy, and XRD. Thin-film characterization by a variety of techniques (optical spectroscopy, specular X-ray reflectivity, atomic force microscopy, X-ray photoelectron spectroscopy, and angle-dependent polarized second harmonic generation) underscore the importance of the chromophore molecular architecture as well as film growth method on film microstructure and optical/electrooptic response.},
doi = {10.1021/ja057556c},
journal = {J. Am. Chem. Soc.},
number = ,
volume = 128,
place = {United States},
year = {Sun Jan 01 00:00:00 EST 2006},
month = {Sun Jan 01 00:00:00 EST 2006}
}