Design and preparation of zwitterionic organic thin films: Self-assembled siloxane-based, thiophene-spaced N-benzylpyridinium dicyanomethanides as nonlinear optical materials

Antonio Facchetti, Milko E. Van der Boom, Alessandro Abbotto, Luca Beverina, Tobin J. Marks*, Giorgo A. Pagani

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

Regioselective alkylation of 1-(4-pyridyl)-2-[5-(dicyanomethanide)thien-2-yl]ethylene sodium salt (2) by a covalently surface-bound benzylhalide (4) produces a polar-ordered zwitterionic thin film (5). Chemisorption of 2 on the coupling layer 4 was monitored by UV-vis spectroscopy, contact-angle measurements, X-ray photoelectron spectroscopy, and second harmonic generation (SHG). Relative to carbanion 2, the film UV-vis spectrum exhibits a red-shifted (Δλ ∼ 170 nm) charge-transfer band, consistent with quaternization of the pyridyl group of 2 by 4. The nonlinear optical properties of the blue films of 5 were measured by SHG. The average molecular tilt angle of the chromophore was determined to be ∼46°, and χZZZ(2) ∼ 5.0 × 10-8 esu (∼20 pm/V) was estimated at a fundamental wavelength of 1064 nm.

Original languageEnglish (US)
Pages (from-to)5939-5942
Number of pages4
JournalLangmuir
Volume17
Issue number19
DOIs
StatePublished - Sep 18 2001

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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