Premium
Extended Alkenyl and Alkynyl Benzotriazoles with Enhanced Two‐Photon Absorption Properties as a Promising Alternative to Benzothiadiazoles
Author(s) -
TorresMoya Iván,
BenitezMartin Carlos,
Donoso Beatriz,
Tardío Carlos,
Martín Raúl,
Carrillo José R.,
DíazOrtiz Ángel,
Najera Francisco,
Prieto Pilar,
PerezInestrosa Ezequiel
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903493
Subject(s) - substituent , fluorescence , absorption (acoustics) , photochemistry , chemistry , two photon absorption , electron donor , acceptor , stokes shift , materials science , stereochemistry , organic chemistry , optics , physics , laser , catalysis , composite material , condensed matter physics
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 S 2 ←S 0 transitions and a high charge‐transfer character. Time‐dependent DFT calculations supported the experimental results.