TY - JOUR
T1 - Covalent assembly of stilbene-based monolayers
T2 - Factors controlling molecular interactions
AU - Shukla, Atindra D.
AU - Strawser, David
AU - Lucassen, Andre C.B.
AU - Freeman, Dalia
AU - Cohen, Hagai
AU - Jose, D. Amilan
AU - Das, Amitava
AU - Evmenenko, Guennadi
AU - Dutta, Pulak
AU - Van Der Boom, Milko E.
PY - 2004/11/11
Y1 - 2004/11/11
N2 - A new series of stilbene-based chromophores have been used to prepare structurally related siloxane-based monolayers in order to determine which factors control the intermolecular chromophore-chromophore interactions in the solid state. The reaction of chromophore precursors 4-styrylpyridine (1), 4-[2-(4bromophenyl)-vinyl]-pyridine (2), 4-(2-naphthalen-1-ylvinyl)-pyridine (3), 4-(2-anthracen-9-ylvinyl)-pyridine (4), and 4-(2-pyren-2-ylvinyl)-pyridine (5) with excess 3-iodo-n-propyl-1-trimethoxysilane resulted in the corresponding salts 6-10 in quantitative yield. The assembly of chromophores 6-10 on hydrophilic substrates from solution resulted in the formation of densely packed monolayers with a film thickness of 1 nm. The average chromophore density (1 chromophore/50 A° 2) is well within the range that allows π-π stacking to occur. Transmission UV-vis spectroscopy of the siloxane-based films shows that the intermolecular interactions are. a function of the aryl groups (e.g., phenyl, bromophenyl, naphthalene, anthracene, and pyrene). Relatively weak electronic interactions occur between the surface-bound chromophores 6, 7, and 10, whereas strong electronic interactions occur between surface-bound chromophores 8 and 9. The series of monolayers on sodium lime glass and polished silicon is characterized by a combination of physicochemical methods including X-ray photoelectron spectroscopy, advancing aqueous contact angle measurements, optical spectroscopy, atomic force microscopy, and synchrotron X-ray reflectivity.
AB - A new series of stilbene-based chromophores have been used to prepare structurally related siloxane-based monolayers in order to determine which factors control the intermolecular chromophore-chromophore interactions in the solid state. The reaction of chromophore precursors 4-styrylpyridine (1), 4-[2-(4bromophenyl)-vinyl]-pyridine (2), 4-(2-naphthalen-1-ylvinyl)-pyridine (3), 4-(2-anthracen-9-ylvinyl)-pyridine (4), and 4-(2-pyren-2-ylvinyl)-pyridine (5) with excess 3-iodo-n-propyl-1-trimethoxysilane resulted in the corresponding salts 6-10 in quantitative yield. The assembly of chromophores 6-10 on hydrophilic substrates from solution resulted in the formation of densely packed monolayers with a film thickness of 1 nm. The average chromophore density (1 chromophore/50 A° 2) is well within the range that allows π-π stacking to occur. Transmission UV-vis spectroscopy of the siloxane-based films shows that the intermolecular interactions are. a function of the aryl groups (e.g., phenyl, bromophenyl, naphthalene, anthracene, and pyrene). Relatively weak electronic interactions occur between the surface-bound chromophores 6, 7, and 10, whereas strong electronic interactions occur between surface-bound chromophores 8 and 9. The series of monolayers on sodium lime glass and polished silicon is characterized by a combination of physicochemical methods including X-ray photoelectron spectroscopy, advancing aqueous contact angle measurements, optical spectroscopy, atomic force microscopy, and synchrotron X-ray reflectivity.
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U2 - 10.1021/jp047358s
DO - 10.1021/jp047358s
M3 - Article
AN - SCOPUS:9144241176
SN - 1520-6106
VL - 108
SP - 17505
EP - 17511
JO - Journal of Physical Chemistry B
JF - Journal of Physical Chemistry B
IS - 45
ER -