Design and preparation of zwitterionic organic thin films

Self-assembled siloxane-based, thiophene-spaced N-benzylpyridinium dicyanomethanides as nonlinear optical materials

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

Research output: Contribution to journalArticle

33 Citations (Scopus)

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
Pages (from-to)5939-5942
Number of pages4
JournalLangmuir
Volume17
Issue number19
DOIs
Publication statusPublished - Sep 18 2001

Fingerprint

Siloxanes
Thiophenes
Optical materials
siloxanes
Thiophene
optical materials
Harmonic generation
thiophenes
harmonic generations
Thin films
preparation
alkylation
Alkylation
Chromophores
Angle measurement
Chemisorption
thin films
Ultraviolet spectroscopy
chemisorption
chromophores

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Colloid and Surface Chemistry

Cite this

Design and preparation of zwitterionic organic thin films : Self-assembled siloxane-based, thiophene-spaced N-benzylpyridinium dicyanomethanides as nonlinear optical materials. / Facchetti, Antonio; van der Boom, Milko; Abbotto, Alessandro; Beverina, Luca; Marks, Tobin J; Pagani, Giorgo A.

In: Langmuir, Vol. 17, No. 19, 18.09.2001, p. 5939-5942.

Research output: Contribution to journalArticle

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