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

Atindra D. Shukla, David Strawser, Andre C.B. Lucassen, Dalia Freeman, Hagai Cohen, D. Amilan Jose, Amitava Das, Guennadi Evmenenko, Pulak Dutta, Milko E. Van Der Boom*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)17505-17511
Number of pages7
JournalJournal of Physical Chemistry B
Volume108
Issue number45
DOIs
StatePublished - Nov 11 2004

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films
  • Materials Chemistry

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