Title

Synthesis Of New Two-Photon Absorbing Fluorene Derivatives Via Cu-Mediated Ullmann Condensations

Title - Alternative

J. Org. Chem.

Keywords

2-Photon; Triarylamines; Substitution; Molecules; Catalysis; Copper; Chemistry, Organic

Abstract

The Ullmann amination reaction was utilized to provide access to a number of fluorene analogues from common intermediates, via facile functionalization at positions 2, 7, and 9 of the fluorene ring. Through variation of amine or iodofluorene derivative, analogues bearing substitutents with varying electron-donating and electron-withdrawing ability, e.g., diphenylamino, bis-(4-methoxyphenyl)amine, nitro, and benzothiazole, were synthesized in good yield. The novel fluorene derivatives were fully characterized, including absorption and emission spectra. Didecylation at the 9-position afforded remarkably soluble derivatives. Target compounds 4, 5, and 9 are potentially useful as fluorophores in two-photon fluorescence microscopy. Their UV-vis spectra display desirable absorption in the range of interest suitable for two-photon excitation by near-IR femtosecond lasers. Preliminary measurements of two-photon absorption indicate the derivatives exhibit high two-photon absorptivity, affirming their potential as two-photon fluorophores. For example, using a 1210 nm femtosecond pump beam, diphenylaminobenzothiazolylfluorene 4 exhibited nondegenerate two-photon absorption, with two-photon absorptivity is) of ca. 820 x 10(-50) cm(4) s photon(-1) molecule(-1) at the femtosecond white light continuum probe wavelength of 615 nm.

Publication Title

Journal of Organic Chemistry

Volume

65

Issue/Number

15

Publication Date

1-1-2000

Document Type

Article

Language

English

First Page

4475

Last Page

4481

WOS Identifier

WOS:000088488900001

ISSN

0022-3263

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