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

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)


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
Pages (from-to)17505-17511
Number of pages7
JournalJournal of Physical Chemistry B
Issue number45
Publication statusPublished - Nov 11 2004

ASJC Scopus subject areas

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

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