Abstract
The synthesis of the heterocycle-based diethanolaminomethyl-functionalized derivative 1-(pyridin-4-yl)-2-[(N-methylpyrrol-2-yl)-5-methylenediethanolamine]ethene (2) from (1-pyridin-4-yl)-2-(N-methyl-pyrrol-2-yl)ethene (1) and their methylpyridinium dyes 1-(N-methylpyridinio)-2-[(N-methylpyrrol-2-yl)-5- methylenediethanolamine]ethene iodide (3) and 1-(N-methylpyridinio)-2-[(N-methylpyrrol-2-yl)-5- methylenediethanolamine]ethene iodide (4) is described. NLO-active chromophore monolayers SA-1 and SA-2 were obtained by reaction of p-iodomethylphenyldiiodochlorosilane (5)-functionalized substrates and dye precursors 1 and 2, respectively. A χ(2) value of ∼120 pm/V is observed for SA-2. The new diethanolaminomethyl-functionalized chromophore 2 is also a suitable building block for the layer-bylayer formation of intrinsically acentric, highly transparent nonlinear optical/electro-optic multilayers (SAS = self-assembled superlattice). The organic SAS films are characterized by a combination of physicochemical methods including synchrotron specular X-ray reflectivity, angle-dependent polarized second-harmonic generation, optical (absorption and photoluminescence) spectroscopy, X-ray photospectroscopy, atomic force microscopy, and advancing contact angle measurements.
| Original language | English |
|---|---|
| Pages (from-to) | 1064-1072 |
| Number of pages | 9 |
| Journal | Chemistry of Materials |
| Volume | 15 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - Mar 11 2003 |
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ASJC Scopus subject areas
- Materials Science(all)
- Materials Chemistry
Cite this
Layer-by-layer self-assembled pyrrole-based donor-acceptor chromophores as electro-optic materials. / Facchetti, Antonio; Abbotto, Alessandro; Beverina, Luca; van der Boom, Milko; Dutta, Pulak; Evmenenko, Guennadi; Pagani, Giorgo A.; Marks, Tobin J.
In: Chemistry of Materials, Vol. 15, No. 5, 11.03.2003, p. 1064-1072.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Layer-by-layer self-assembled pyrrole-based donor-acceptor chromophores as electro-optic materials
AU - Facchetti, Antonio
AU - Abbotto, Alessandro
AU - Beverina, Luca
AU - van der Boom, Milko
AU - Dutta, Pulak
AU - Evmenenko, Guennadi
AU - Pagani, Giorgo A.
AU - Marks, Tobin J
PY - 2003/3/11
Y1 - 2003/3/11
N2 - The synthesis of the heterocycle-based diethanolaminomethyl-functionalized derivative 1-(pyridin-4-yl)-2-[(N-methylpyrrol-2-yl)-5-methylenediethanolamine]ethene (2) from (1-pyridin-4-yl)-2-(N-methyl-pyrrol-2-yl)ethene (1) and their methylpyridinium dyes 1-(N-methylpyridinio)-2-[(N-methylpyrrol-2-yl)-5- methylenediethanolamine]ethene iodide (3) and 1-(N-methylpyridinio)-2-[(N-methylpyrrol-2-yl)-5- methylenediethanolamine]ethene iodide (4) is described. NLO-active chromophore monolayers SA-1 and SA-2 were obtained by reaction of p-iodomethylphenyldiiodochlorosilane (5)-functionalized substrates and dye precursors 1 and 2, respectively. A χ(2) value of ∼120 pm/V is observed for SA-2. The new diethanolaminomethyl-functionalized chromophore 2 is also a suitable building block for the layer-bylayer formation of intrinsically acentric, highly transparent nonlinear optical/electro-optic multilayers (SAS = self-assembled superlattice). The organic SAS films are characterized by a combination of physicochemical methods including synchrotron specular X-ray reflectivity, angle-dependent polarized second-harmonic generation, optical (absorption and photoluminescence) spectroscopy, X-ray photospectroscopy, atomic force microscopy, and advancing contact angle measurements.
AB - The synthesis of the heterocycle-based diethanolaminomethyl-functionalized derivative 1-(pyridin-4-yl)-2-[(N-methylpyrrol-2-yl)-5-methylenediethanolamine]ethene (2) from (1-pyridin-4-yl)-2-(N-methyl-pyrrol-2-yl)ethene (1) and their methylpyridinium dyes 1-(N-methylpyridinio)-2-[(N-methylpyrrol-2-yl)-5- methylenediethanolamine]ethene iodide (3) and 1-(N-methylpyridinio)-2-[(N-methylpyrrol-2-yl)-5- methylenediethanolamine]ethene iodide (4) is described. NLO-active chromophore monolayers SA-1 and SA-2 were obtained by reaction of p-iodomethylphenyldiiodochlorosilane (5)-functionalized substrates and dye precursors 1 and 2, respectively. A χ(2) value of ∼120 pm/V is observed for SA-2. The new diethanolaminomethyl-functionalized chromophore 2 is also a suitable building block for the layer-bylayer formation of intrinsically acentric, highly transparent nonlinear optical/electro-optic multilayers (SAS = self-assembled superlattice). The organic SAS films are characterized by a combination of physicochemical methods including synchrotron specular X-ray reflectivity, angle-dependent polarized second-harmonic generation, optical (absorption and photoluminescence) spectroscopy, X-ray photospectroscopy, atomic force microscopy, and advancing contact angle measurements.
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U2 - 10.1021/cm020929d
DO - 10.1021/cm020929d
M3 - Article
VL - 15
SP - 1064
EP - 1072
JO - Chemistry of Materials
JF - Chemistry of Materials
SN - 0897-4756
IS - 5
ER -