New sulfonyl-containing materials for nonlinear optics: Semiempirical calculations, synthesis, and properties

Abraham Ulman, Craig S. Willand, Werner Köhler, Douglas R. Robello, David J. Williams, Laura Handley

Research output: Contribution to journalArticle

Abstract

In this study we describe semiempirical calculations, synthesis, ground-state dipole moment measurements, and measurements of molecular second-order hyperpolarizability coefficients (β) for new stilbene and azobenzene derivatives containing a methylsulfonyl group as the electron acceptor. We show that theoretical calculations can be used to predict the trends for molecular hyperpolarizabilities between similar compounds and that these gas-phase calculations underestimate β values, probably as a result of the valence basis set used in the calculations. Whereas the sulfone group has been demonstrated to give molecular hyperpolarizabilities somewhat less than those of similar nitro compounds, the difference becomes less as the degree of conjugation is increased. The increased transparency in the visible spectrum and the synthetic flexibility may make sulfonyl compounds important for some applications.

Original languageEnglish (US)
Pages (from-to)7083-7090
Number of pages8
JournalJournal of the American Chemical Society
Volume112
Issue number20
StatePublished - 1990

Fingerprint

Nitro Compounds
Stilbenes
Nonlinear optics
Sulfones
Gases
Electrons
Azobenzene
Dipole moment
Transparency
Ground state
Derivatives
azobenzene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ulman, A., Willand, C. S., Köhler, W., Robello, D. R., Williams, D. J., & Handley, L. (1990). New sulfonyl-containing materials for nonlinear optics: Semiempirical calculations, synthesis, and properties. Journal of the American Chemical Society, 112(20), 7083-7090.

New sulfonyl-containing materials for nonlinear optics : Semiempirical calculations, synthesis, and properties. / Ulman, Abraham; Willand, Craig S.; Köhler, Werner; Robello, Douglas R.; Williams, David J.; Handley, Laura.

In: Journal of the American Chemical Society, Vol. 112, No. 20, 1990, p. 7083-7090.

Research output: Contribution to journalArticle

Ulman, A, Willand, CS, Köhler, W, Robello, DR, Williams, DJ & Handley, L 1990, 'New sulfonyl-containing materials for nonlinear optics: Semiempirical calculations, synthesis, and properties', Journal of the American Chemical Society, vol. 112, no. 20, pp. 7083-7090.
Ulman, Abraham ; Willand, Craig S. ; Köhler, Werner ; Robello, Douglas R. ; Williams, David J. ; Handley, Laura. / New sulfonyl-containing materials for nonlinear optics : Semiempirical calculations, synthesis, and properties. In: Journal of the American Chemical Society. 1990 ; Vol. 112, No. 20. pp. 7083-7090.
@article{e462c549c3194a7481cc2e1084db0c01,
title = "New sulfonyl-containing materials for nonlinear optics: Semiempirical calculations, synthesis, and properties",
abstract = "In this study we describe semiempirical calculations, synthesis, ground-state dipole moment measurements, and measurements of molecular second-order hyperpolarizability coefficients (β) for new stilbene and azobenzene derivatives containing a methylsulfonyl group as the electron acceptor. We show that theoretical calculations can be used to predict the trends for molecular hyperpolarizabilities between similar compounds and that these gas-phase calculations underestimate β values, probably as a result of the valence basis set used in the calculations. Whereas the sulfone group has been demonstrated to give molecular hyperpolarizabilities somewhat less than those of similar nitro compounds, the difference becomes less as the degree of conjugation is increased. The increased transparency in the visible spectrum and the synthetic flexibility may make sulfonyl compounds important for some applications.",
author = "Abraham Ulman and Willand, {Craig S.} and Werner K{\"o}hler and Robello, {Douglas R.} and Williams, {David J.} and Laura Handley",
year = "1990",
language = "English (US)",
volume = "112",
pages = "7083--7090",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

T1 - New sulfonyl-containing materials for nonlinear optics

T2 - Semiempirical calculations, synthesis, and properties

AU - Ulman, Abraham

AU - Willand, Craig S.

AU - Köhler, Werner

AU - Robello, Douglas R.

AU - Williams, David J.

AU - Handley, Laura

PY - 1990

Y1 - 1990

N2 - In this study we describe semiempirical calculations, synthesis, ground-state dipole moment measurements, and measurements of molecular second-order hyperpolarizability coefficients (β) for new stilbene and azobenzene derivatives containing a methylsulfonyl group as the electron acceptor. We show that theoretical calculations can be used to predict the trends for molecular hyperpolarizabilities between similar compounds and that these gas-phase calculations underestimate β values, probably as a result of the valence basis set used in the calculations. Whereas the sulfone group has been demonstrated to give molecular hyperpolarizabilities somewhat less than those of similar nitro compounds, the difference becomes less as the degree of conjugation is increased. The increased transparency in the visible spectrum and the synthetic flexibility may make sulfonyl compounds important for some applications.

AB - In this study we describe semiempirical calculations, synthesis, ground-state dipole moment measurements, and measurements of molecular second-order hyperpolarizability coefficients (β) for new stilbene and azobenzene derivatives containing a methylsulfonyl group as the electron acceptor. We show that theoretical calculations can be used to predict the trends for molecular hyperpolarizabilities between similar compounds and that these gas-phase calculations underestimate β values, probably as a result of the valence basis set used in the calculations. Whereas the sulfone group has been demonstrated to give molecular hyperpolarizabilities somewhat less than those of similar nitro compounds, the difference becomes less as the degree of conjugation is increased. The increased transparency in the visible spectrum and the synthetic flexibility may make sulfonyl compounds important for some applications.

UR - http://www.scopus.com/inward/record.url?scp=0001703345&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001703345&partnerID=8YFLogxK

M3 - Article

VL - 112

SP - 7083

EP - 7090

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 20

ER -