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π-Expanded α,β-unsaturated ketones: Synthesis, optical properties, and two-photon-induced polymerization

Research output: Contribution to journalArticleScientificpeer-review

Details

Original languageEnglish
Pages (from-to)682–690
Number of pages9
JournalChemPhysChem
Volume16
Issue number3
DOIs
Publication statusPublished - 2015
Publication typeA1 Journal article-refereed

Abstract

A library of π-expanded α,β-unsaturated ketones was designed and synthesized. They were prepared by a combination of Wittig reaction, Sonogashira reaction, and aldol condensation. It was further demonstrated that the double aldol condensation can be performed effectively for highly polarized styrene- and diphenylacetylene-derived aldehydes. The strategic placement of two dialkylamino groups at the periphery of D-π-A-π-D molecules resulted in dyes with excellent solubility. These ketones absorb light in the region 400-550nm. Many of them display strong solvatochromism so that the emission ranges from 530-580nm in toluene to the near-IR region in benzonitrile. Ketones based on cyclobutanone as central moieties display very high fluorescence quantum yields in nonpolar solvents, which decrease drastically in polar media. Photophysical studies of these new functional dyes revealed that they possess an enhanced two-photon absorption cross section when compared with simpler ketone derivatives. Due to strong polarization of the resulting dyes, values of two-photon absorption cross sections on the level of 200-300GM at 800nm were achieved, and thanks to that as well as the presence of the keto group, these new two-photon initiators display excellent performance so that the operating region is 5-75mW in some cases.

Keywords

  • Aldol reaction, Ketones, Photosensitizers, Polymerization, Two-photon absorption

Publication forum classification

Field of science, Statistics Finland