Title

Design, Synthesis, And Structural And Spectroscopic Studies Of Push-Pull Two-Photon Absorbing Chromophores With Acceptor Groups Of Varying Strength

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. © 2013 American Chemical Society.

Publication Date

2-1-2013

Publication Title

Journal of Organic Chemistry

Volume

78

Issue

3

Number of Pages

1014-1025

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/jo302423p

Socpus ID

84873369133 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/84873369133

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