Covalent assembly of stilbene-based monolayers: factors controlling molecular interactions

Shukla, Atindra D. ; Strawser, David ; Lucassen, Andre C. B. ; Freeman, Dalia ; Cohen, Hagai ; Amilan Jose, D. ; Das, Amitava ; Evmenenko, Guennadi ; Dutta, Pulak ; van der Boom, Milko E. (2004) Covalent assembly of stilbene-based monolayers: factors controlling molecular interactions The Journal of Physical Chemistry B, 108 (45). pp. 17505-17511. ISSN 1089-5647

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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-(4-bromophenyl)-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 Å2) 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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:59904
Deposited On:07 Sep 2011 14:18
Last Modified:07 Sep 2011 14:18

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