Extended Alkenyl and Alkynyl Benzotriazoles with Enhanced Two‐Photon Absorption Properties as a Promising Alternative to Benzothiadiazoles. Issue 68 (4th November 2019)

• Record Type: Journal Article
• Authors: Torres‐Moya, Iván; Benitez‐Martin, Carlos; Donoso, Beatriz; Tardío, Carlos; Martín, Raúl; Carrillo, José R.; Díaz‐Ortiz, Ángel; Najera, Francisco; Prieto, Pilar; Perez‐Inestrosa, Ezequiel
• Is Part Of: Chemistry. Volume 25:Issue 68(2019)
• Page Start: 15572
• Page End: 15579
• Publication Date: 2019-11-04
• Subjects: density functional calculations -- dyes/pigments -- donor–acceptor systems -- fluorescence -- structure–activity relationships; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201903493
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A series of donor–π–acceptor–π–donor (D ‐π‐A‐π‐D) benzoazole dyes with 2 H ‐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. Abstract : Comparing cores : Promising benzotriazole derivatives with improved electron‐withdrawing properties reveal exceptional photophysical properties. A study of their structure–property relationship reveals tunable high brightness and great cross sections.