Synthetic strategies to derivatizable triphenylamines displaying high two-photon absorption.
A versatile synthetic strategy to access a set of highly fluorescent pi-conjugated triphenylamines bearing a functional linker at various positions on one phenyl ring is described. These compounds were designed for large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatized trisformylated or trisiodinated intermediates described herein allow introduction of a large variety of electron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable for coupling to biomolecules. The monoderivatized three-branched compounds and in particular the benzothiazole (TP-3Bz) series show remarkable linear (high extinction coefficients and high quantum yield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence of functional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branched derivatives also appear to be valuable candidates. Altogether the good optical properties of the new derivatizable pi-conjugated TPA combined with their small size and their compatibility with bioconjugation protocols suggest that they represent a new chemical class of labels potentially applicable for the tracking of biomolecules using two-photon scanning microscopy.
Lartia
Rémy
R
Institut Curie, CNRS UMR-176, bat 110, Centre Universitaire, 91405 Orsay Cedex, France,
Allain
Clémence
C
Bordeau
Guillaume
G
Schmidt
Falk
F
Fiorini-Debuisschert
Céline
C
Charra
Fabrice
F
Teulade-Fichou
Marie-Paule
MP
D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D017785:Photons
D000814:Aniline Compounds