Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

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• 作者：R&eacute ; my Lartia ; Cl&eacute ; mence Allain ; Guillaume Bordeau ; Falk Schmidt ; C&eacute ; line Fiorini-Debuisschert ; Fabrice Charra ; Marie-Paule Teulade-Fichou
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：March 7, 2008
• 年：2008
• 卷：73
• 期：5
• 页码：1732 - 1744
• 全文大小：295K
• 年卷期：v.73,no.5(March 7, 2008)
• ISSN：1520-6904

文摘

<TR>A versatile synthetic strategy to access a set of highly fluorescent -conjugated triphenylamines bearinga functional linker at various positions on one phenyl ring is described. These compounds were designedfor large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatizedtrisformylated or trisiodinated intermediates described herein allow introduction of a large variety ofelectron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable forcoupling to biomolecules. The monoderivatized three-branched compounds and in particular thebenzothiazole (TP-3Bz) series show remarkable linear (high extinction coefficients and high quantumyield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence offunctional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branchedderivatives also appear to be valuable candidates. Altogether the good optical properties of the newderivatizable -conjugated TPA combined with their small size and their compatibility with bioconjugationprotocols suggest that they represent a new chemical class of labels potentially applicable for the trackingof biomolecules using two-photon scanning microscopy.