Strategies for electrooptic film fabrication. Influence of pyrrole-pyridine-based dibranched chromophore architecture on covalent self-assembly, thin-film microstructure, and nonlinear optical response

Antonio Facchetti, Luca Beverina, Milko van der Boom, Pulak Dutta, Guennadi Evmenenko, Atindra D. Shukla, Charlotte E. Stern, Giorgio A. Pagani, Tobin J Marks

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

The new dibranched, heterocyclic "push-pull" chromophores bis{1-(pyridin-4-yl)-2-[2-(N-methyl-pyrrol-5-yl)]ethane}methane (1), 1-(pyrid-4-yl)-2-(N-methyl-5-formylpyrrol-2-yl)ethylene (2), {1-(N-methylpyridinium-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane} {(1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane}-methane (3), N-methyl-2-[1-(N-methylpyrid-4-yl)ethen-2-yl]-5-[pyrid-4-yl]ethen-2-yl]pyrrole iodide (4), bis-{1-(N-methyl-4-pyridinio)-2-[2-(N-methylpyrrol-5-yl)]ethane} 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.

Original languageEnglish
Pages (from-to)2142-2153
Number of pages12
JournalJournal of the American Chemical Society
Volume128
Issue number6
DOIs
Publication statusPublished - Feb 15 2006

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Pyrroles
Ethane
Chromophores
Electrooptical effects
Pyridine
Self assembly
Methane
Iodides
Fabrication
Thin films
Microstructure
Photoelectron Spectroscopy
Atomic Force Microscopy
Film growth
Harmonic generation
Molecular Structure
Molecular structure
Monolayers
Atomic force microscopy
Spectrum Analysis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Strategies for electrooptic film fabrication. Influence of pyrrole-pyridine-based dibranched chromophore architecture on covalent self-assembly, thin-film microstructure, and nonlinear optical response. / Facchetti, Antonio; Beverina, Luca; van der Boom, Milko; Dutta, Pulak; Evmenenko, Guennadi; Shukla, Atindra D.; Stern, Charlotte E.; Pagani, Giorgio A.; Marks, Tobin J.

In: Journal of the American Chemical Society, Vol. 128, No. 6, 15.02.2006, p. 2142-2153.

Research output: Contribution to journalArticle

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abstract = "The new dibranched, heterocyclic {"}push-pull{"} chromophores bis{1-(pyridin-4-yl)-2-[2-(N-methyl-pyrrol-5-yl)]ethane}methane (1), 1-(pyrid-4-yl)-2-(N-methyl-5-formylpyrrol-2-yl)ethylene (2), {1-(N-methylpyridinium-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane} {(1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane}-methane (3), N-methyl-2-[1-(N-methylpyrid-4-yl)ethen-2-yl]-5-[pyrid-4-yl]ethen-2-yl]pyrrole iodide (4), bis-{1-(N-methyl-4-pyridinio)-2-[2-(N-methylpyrrol-5-yl)]ethane} 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.",
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AU - Facchetti, Antonio

AU - Beverina, Luca

AU - van der Boom, Milko

AU - Dutta, Pulak

AU - Evmenenko, Guennadi

AU - Shukla, Atindra D.

AU - Stern, Charlotte E.

AU - Pagani, Giorgio A.

AU - Marks, Tobin J

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