Design, synthesis, and structural and spectroscopic studies of push-pull two-photon absorbing chromophores with acceptor groups of varying strength

Alma R. Morales, Andrew Frazer, Adam W. Woodward, Hyo Yang Ahn-White, Alexandr Fonari, Paul Tongwa, Tatiana Timofeeva, Kevin D. Belfield

Research output: Contribution to journalArticlepeer-review

76 Scopus citations

Abstract

A new series of unsymmetrical diphenylaminofluorene-based chromophores with various strong π-electron acceptors were synthesized and fully characterized. The systematic alteration of the structural design facilitated the investigation of effects such as molecular symmetry and strength of electron-donating and/or -withdrawing termini have on optical nonlinearity. In order to determine the electronic and geometrical properties of the novel compounds, a thorough investigation was carried out by a combination of linear and nonlinear spectroscopic techniques, single-crystal X-ray diffraction, and quantum chemical calculations. Finally, on the basis of two-photon absorption (2PA) cross sections, the general trend for π-electron accepting ability, i.e., ability to accept charge transfer from diphenylamine was: 2-pyran-4-ylidene malononitrile (pyranone) > dicyanovinyl > bis(dicyanomethylidene)indane >1-(thiophen-2-yl)propenone > dicyanoethylenyl >3-(thiophen-2-yl)propenone. An analogue with the 2-pyran-4-ylidene malononitrile acceptor group exhibited a nearly 3-fold enhancement of the 2PA cross section (1650 GM at 840 nm), relative to other members of the series.

Original languageEnglish (US)
Pages (from-to)1014-1025
Number of pages12
JournalJournal of Organic Chemistry
Volume78
Issue number3
DOIs
StatePublished - Feb 1 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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