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 van der Boom

Research output: Contribution to journalArticle

28 Citations (Scopus)

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
Pages (from-to)17505-17511
Number of pages7
JournalJournal of Physical Chemistry B
Volume108
Issue number45
DOIs
Publication statusPublished - Nov 11 2004

Fingerprint

Stilbenes
stilbene
Molecular interactions
molecular interactions
Chromophores
chromophores
Monolayers
assembly
Pyridine
pyridines
Siloxanes
siloxanes
interactions
Anthracene
Pyrene
calcium oxides
Silicon
pyrenes
Naphthalene
Angle measurement

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Shukla, A. D., Strawser, D., Lucassen, A. C. B., Freeman, D., Cohen, H., Jose, D. A., ... van der Boom, M. (2004). Covalent assembly of stilbene-based monolayers: Factors controlling molecular interactions. Journal of Physical Chemistry B, 108(45), 17505-17511. https://doi.org/10.1021/jp047358s

Covalent assembly of stilbene-based monolayers : Factors controlling molecular interactions. / Shukla, Atindra D.; Strawser, David; Lucassen, Andre C B; Freeman, Dalia; Cohen, Hagai; Jose, D. Amilan; Das, Amitava; Evmenenko, Guennadi; Dutta, Pulak; van der Boom, Milko.

In: Journal of Physical Chemistry B, Vol. 108, No. 45, 11.11.2004, p. 17505-17511.

Research output: Contribution to journalArticle

Shukla, AD, Strawser, D, Lucassen, ACB, Freeman, D, Cohen, H, Jose, DA, Das, A, Evmenenko, G, Dutta, P & van der Boom, M 2004, 'Covalent assembly of stilbene-based monolayers: Factors controlling molecular interactions', Journal of Physical Chemistry B, vol. 108, no. 45, pp. 17505-17511. https://doi.org/10.1021/jp047358s
Shukla AD, Strawser D, Lucassen ACB, Freeman D, Cohen H, Jose DA et al. Covalent assembly of stilbene-based monolayers: Factors controlling molecular interactions. Journal of Physical Chemistry B. 2004 Nov 11;108(45):17505-17511. https://doi.org/10.1021/jp047358s
Shukla, Atindra D. ; Strawser, David ; Lucassen, Andre C B ; Freeman, Dalia ; Cohen, Hagai ; Jose, D. Amilan ; Das, Amitava ; Evmenenko, Guennadi ; Dutta, Pulak ; van der Boom, Milko. / Covalent assembly of stilbene-based monolayers : Factors controlling molecular interactions. In: Journal of Physical Chemistry B. 2004 ; Vol. 108, No. 45. pp. 17505-17511.
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