Extended Alkenyl and Alkynyl Benzotriazoles with Enhanced Two-Photon Absorption Properties as a Promising Alternative to Benzothiadiazoles

Abstract

A series of donor–π–acceptor–π–donor (D-π-A-π-D) benzoazole dyes with 2H-benzo[d][1,2,3]triazole or BTD cores have been prepared and their photophysical properties characterized. The properties of these compounds display remarkable differences, mainly as a result of the electron-donor substituent. Dyes with the best properties have visible-light absorption over λ=400 nm, large Stokes shifts in the range of about 3500–6400 cm−1, and good fluorescence emission with quantum yields of up to 0.78. The two-photon absorption properties were also studied to establish the relationship between structure and properties in the different compounds synthesized. These results provided cross sections of up to 1500 GM, with a predominance of S2←S0 transitions and a high charge-transfer character. Time-dependent DFT calculations supported the experimental results.