Push-pull arylethynyl porphyrins: New chromophores that exhibited large molecular first-order hyperpolarizabilities

S. M. LeCours, H. W. Guan, Stephen DiMagno, C. H. Wang, M. J. Therien

Research output: Contribution to journalArticle

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Abstract

A new class of chromophores has been fabricated that features both electron-releasing and electron-withdrawing groups fused via an intervening ethynyl moiety to the carbon framework of a (porphinato)metal complex. These species possess large molecular first-order hyperpolarizabilities (β). We report herein the synthesis, optical spectroscopy, and the hyper-Rayleigh scattering data used to determine the β values of two archetypal members of this new class of exceptional nonlinear chromophores: [5-[[4'-(dimethylamino)phenyl]ethynyl]-15-[(4''-nitrophenyl)ethynyl]-1 0,20-diphenylporphinato]copper(II) and [5-[[4'-(dimethylamino)phenyl]ethynyl]-15-[(4''-nitrophenyl)ethynyl]-1 0,20-diphenyl]porphinato]zinc(II). One of these compounds, [5-[[4'-(dimethylamino)phenyl]ethynyl]-15-[(4''-nitrophenyl)ethynyl]-1 0,20-diphenylporphinato]zinc(II), possesses β values near 5000 x 10-30 esu at incident irradiation wavelengths of both 830 and 1064 nm. These studies suggest that this chromophoric structural motif may find utility in the development of electrooptic devices as well as materials for efficient frequency doubling of incident irradiation (second harmonic generation).

Original languageEnglish (US)
Pages (from-to)1497-1503
Number of pages7
JournalJournal of the American Chemical Society
Volume118
Issue number6
DOIs
StatePublished - Jan 1 1996

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Porphyrins
Chromophores
Zinc
Irradiation
Rayleigh scattering
Electrons
Electrooptical effects
Harmonic generation
Metal complexes
Coordination Complexes
Copper
Wavelength
Carbon
Spectrum Analysis
Equipment and Supplies
4-nitrophenyl
Optical spectroscopy

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Push-pull arylethynyl porphyrins : New chromophores that exhibited large molecular first-order hyperpolarizabilities. / LeCours, S. M.; Guan, H. W.; DiMagno, Stephen; Wang, C. H.; Therien, M. J.

In: Journal of the American Chemical Society, Vol. 118, No. 6, 01.01.1996, p. 1497-1503.

Research output: Contribution to journalArticle

LeCours, S. M. ; Guan, H. W. ; DiMagno, Stephen ; Wang, C. H. ; Therien, M. J. / Push-pull arylethynyl porphyrins : New chromophores that exhibited large molecular first-order hyperpolarizabilities. In: Journal of the American Chemical Society. 1996 ; Vol. 118, No. 6. pp. 1497-1503.
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