Related Experiment Video
Updated: Mar 22, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Non-radiative processes in protonated diazines, pyrimidine bases and an aromatic azine
Gustavo A Pino1, Géraldine Feraud2, Michel Broquier3
1Instituto de Investigaciones en Físico Química de Córdoba (INFIQC) CONICET - UNC. Dpto. de Fisicoquímica - Facultad de Ciencias Químicas - Centro Láser de Ciencias Moleculares - Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina.
Abstract:
The excited state lifetimes of DNA bases are often very short due to very efficient non-radiative processes assigned to the ππ*-nπ* coupling. A set of protonated aromatic diazine molecules (pyridazine, pyrimidine and pyrazine C4H5N2(+)) and protonated pyrimidine DNA bases (cytosine, uracil and thymine), as well as the protonated pyridine (C5H6N(+)), have been investigated. For all these molecules except one tautomer of protonated uracil (enol-keto), electronic spectroscopy exhibits vibrational line broadening. Excited state geometry optimization at the CC2 level has been conducted to find out whether the excited state lifetimes measured from line broadening can be correlated to the calculated ordering of the ππ* and nπ* states and the ππ*-nπ* energy gap. The short lifetimes, observed when one nitrogen atom of the ring is not protonated, can be rationalized by relaxation of the ππ* state to the nπ* state or directly to the electronic ground state through ring puckering.
More Related Videos
Related Concept Videos
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution: –OH and –H
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Basicity of Heterocyclic Aromatic Amines

