Abstract
A series of inexpensive and water-soluble fluorescent dihydro-[1,2,4]triazolo [4,3-a]pyridin-2-ium-carboxylates (Safirinium dyes) have been synthesized and characterized by UV–Vis, IR, 1H- and 13C NMR spectroscopic techniques as well as by single crystal X-ray analysis. Significantly lower fluorescence quantum yields were determined in aprotic polar solvent (DMF). The photophysical properties of zwitterions and hydrochlorides were rationalized theoretically. A combined experimental and DFT/TD-DFT study of absorption and emission spectra have been performed. The calculations were carried out within the vertical non-equilibrium approximation or the state-specific approach using conventional (APFD, B3LYP and PBE0) and long-range-corrected hybrid functionals (CAM-B3LYP and ωB97XD) by means PCM and SMD solvation models. We have found that global hybrid functionals (GH) fail for charge transfer excited states in which charge is moved from the substituent to the heteroaromatic system, while the long range corrected functionals deliver consistent estimates, especially within the state-specific PCM modeling framework. The long-range-corrected hybrid functionals (RSH) were also found to be the most efficient in reproducing the emissive properties of the dyes.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
