Molecular hyperpolarizabilities of barbituric acid and cyclobutene-1,2- dione derivatives. Electronic and steric effects

Bong-Rae Cho, Jong Tae Je, Seung Jae Lee, Sang Hae Lee, Hyun Soo Kim, Seung-Joon Jeon, Ok Keun Song, C. H. Wang

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A series of merocyanine dyes containing various donors and barbituric acid and cyclobutene-1,2-dione moieties as the acceptors have been synthesized and their first-order hyperpolarizabilities β were determined. The β values of barbituric acid derivatives increase as the strength of the donor is increased from 4-dimethylaminophenyl to trimethylindolinyl to benzothiazolinyl, apparently due to the gradual decrease in the bond length alternation (BLA) from a large positive value to an optimum one by a stronger donor. In contrast, the β values for the cyclobutene-1,2-dione derivatives decrease with the same variation of the donors even though the cyclobutene-1,2-dione is a poorer acceptor than the barbituric acid moiety. The results have been attributed to the electron-donating ability of the donors and the increased distortion of the chromophores from planarity.

Original languageEnglish
Pages (from-to)2141-2144
Number of pages4
JournalJournal of the Chemical Society. Perkin Transactions 2
Volume10
Publication statusPublished - 1996 Oct 1

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Derivatives
Bond length
Chromophores
Electrons
3-cyclobutene-1,2-dione
barbituric acid
merocyanine dye

ASJC Scopus subject areas

  • Chemistry(all)

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Molecular hyperpolarizabilities of barbituric acid and cyclobutene-1,2- dione derivatives. Electronic and steric effects. / Cho, Bong-Rae; Je, Jong Tae; Lee, Seung Jae; Lee, Sang Hae; Kim, Hyun Soo; Jeon, Seung-Joon; Song, Ok Keun; Wang, C. H.

In: Journal of the Chemical Society. Perkin Transactions 2, Vol. 10, 01.10.1996, p. 2141-2144.

Research output: Contribution to journalArticle

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AU - Lee, Sang Hae

AU - Kim, Hyun Soo

AU - Jeon, Seung-Joon

AU - Song, Ok Keun

AU - Wang, C. H.

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AB - A series of merocyanine dyes containing various donors and barbituric acid and cyclobutene-1,2-dione moieties as the acceptors have been synthesized and their first-order hyperpolarizabilities β were determined. The β values of barbituric acid derivatives increase as the strength of the donor is increased from 4-dimethylaminophenyl to trimethylindolinyl to benzothiazolinyl, apparently due to the gradual decrease in the bond length alternation (BLA) from a large positive value to an optimum one by a stronger donor. In contrast, the β values for the cyclobutene-1,2-dione derivatives decrease with the same variation of the donors even though the cyclobutene-1,2-dione is a poorer acceptor than the barbituric acid moiety. The results have been attributed to the electron-donating ability of the donors and the increased distortion of the chromophores from planarity.

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