TY - JOUR
T1 - Fluorescent property of 3-hydroxymethyl imidazo[1,2-a]pyridine and pyrimidine derivatives
AU - Velázquez-Olvera, Stephania
AU - Salgado-Zamora, Héctor
AU - Velázquez-Ponce, Manuel
AU - Campos-Aldrete, Elena
AU - Reyes-Arellano, Alicia
AU - Pérez-González, Cuauhtémoc
N1 - Funding Information:
We thank Consejo Nacional de Ciencia y Tecnología Mexico for financial support through project 49937. We are grateful to Dr. Armando Gómez Poyou, Instituto de Fisiología Celular, Universidad Nacional Autónoma de México for the fluorometric measurements. Special thanks to Miguel Angel Canseco Martínez, Investigación en Materiales, Universidad Nacional Autónoma de México for the thermogravimetric study. SVO thanks Consejo Nacional de Ciencia y Tecnología for graduate scholarship No. 257526.
PY - 2012/8/7
Y1 - 2012/8/7
N2 - Background: Imidazo[1,2-a]pyridines and pyrimidines are important organic fluorophores which have been investigated as biomarkers and photochemical sensors. The effect on the luminescent property by substituents in the heterocycle and phenyl rings, have been studied as well. In this investigation, series of 3-hydroxymethyl imidazo[1,2-a]pyridines and pyrimidines were synthesized and evaluated in relation to fluorescence emission, based upon the hypothesis that the hydroxymethyl group may act as an enhancer of fluorescence intensity. Results: Compounds of both series emitted light in organic solvents dilutions as well as in acidic and alkaline media. Quantitative fluorescence spectroscopy determined that both fused heterocycles fluoresced more intensely than the parent unsubstituted imidazo[1,2-a]azine fluorophore. In particular, 3-hydroxymethyl imidazo[1,2-a]pyridines fluoresced more intensely than 3-hydroxymethyl imidazo[1,2-a]pyrimidines, the latter emitting blue light at longer wavelengths, whereas the former emitted purple light.Conclusion: It was concluded that in most cases the hydroxymethyl moiety did act as an enhancer of the fluorescence intensity, however, a comparison made with the fluorescence emitted by 2-aryl imidazo[1,2-a]azines revealed that in some cases the hydroxymethyl substituent decreased the fluorescence intensity.
AB - Background: Imidazo[1,2-a]pyridines and pyrimidines are important organic fluorophores which have been investigated as biomarkers and photochemical sensors. The effect on the luminescent property by substituents in the heterocycle and phenyl rings, have been studied as well. In this investigation, series of 3-hydroxymethyl imidazo[1,2-a]pyridines and pyrimidines were synthesized and evaluated in relation to fluorescence emission, based upon the hypothesis that the hydroxymethyl group may act as an enhancer of fluorescence intensity. Results: Compounds of both series emitted light in organic solvents dilutions as well as in acidic and alkaline media. Quantitative fluorescence spectroscopy determined that both fused heterocycles fluoresced more intensely than the parent unsubstituted imidazo[1,2-a]azine fluorophore. In particular, 3-hydroxymethyl imidazo[1,2-a]pyridines fluoresced more intensely than 3-hydroxymethyl imidazo[1,2-a]pyrimidines, the latter emitting blue light at longer wavelengths, whereas the former emitted purple light.Conclusion: It was concluded that in most cases the hydroxymethyl moiety did act as an enhancer of the fluorescence intensity, however, a comparison made with the fluorescence emitted by 2-aryl imidazo[1,2-a]azines revealed that in some cases the hydroxymethyl substituent decreased the fluorescence intensity.
UR - http://www.scopus.com/inward/record.url?scp=84872262580&partnerID=8YFLogxK
U2 - 10.1186/1752-153X-6-83
DO - 10.1186/1752-153X-6-83
M3 - Artículo
C2 - 22871219
SN - 1752-153X
VL - 6
JO - Chemistry Central Journal
JF - Chemistry Central Journal
IS - 1
M1 - 83
ER -