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
DOIs
Publication statusPublished - 1996 Oct

ASJC Scopus subject areas

  • Chemistry(all)

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