TY - JOUR
T1 - 3(2H)-Furanone as a promising scaffold for the synthesis of novel fluorescent organic dyes
T2 - An experimental and theoretical investigation
AU - Varghese, Beena
AU - Al-Busafi, Saleh N.
AU - Suliman, Fakhreldin O.
AU - Al-Kindy, Salma M.Z.
N1 - Publisher Copyright:
© 2015 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
PY - 2015/8/1
Y1 - 2015/8/1
N2 - 3(2H)-Furanones are a type of five-membered heterocyclic compounds of synthetic and biological importance. For exploring the utilities of this "sweet" aroma component for bio-analytical purposes we have prepared and characterized two novel fluorophores (2Z)-2-(5-fluoro-2-ntro benzylidene)-5-phenyl-3(2H)-furanone (FNPF) and (2Z)-2-(4-carboxy benzylidene)-5-phenyl-3-(2H)-furanone (CBPF) on a 3-furanone skeleton. In order to expand their application potential, the photophysical properties have been investigated using absorption and emission spectroscopy, in combination with quantum chemical calculations. As expected, both compounds showed efficient solvatochromic properties and the excited state dipole moments are larger than those of the ground state. Solvent dependent spectral data using TD-DFT calculations on the optimized ground and excited state structures of both compounds were found to correlate well with the experimental findings.
AB - 3(2H)-Furanones are a type of five-membered heterocyclic compounds of synthetic and biological importance. For exploring the utilities of this "sweet" aroma component for bio-analytical purposes we have prepared and characterized two novel fluorophores (2Z)-2-(5-fluoro-2-ntro benzylidene)-5-phenyl-3(2H)-furanone (FNPF) and (2Z)-2-(4-carboxy benzylidene)-5-phenyl-3-(2H)-furanone (CBPF) on a 3-furanone skeleton. In order to expand their application potential, the photophysical properties have been investigated using absorption and emission spectroscopy, in combination with quantum chemical calculations. As expected, both compounds showed efficient solvatochromic properties and the excited state dipole moments are larger than those of the ground state. Solvent dependent spectral data using TD-DFT calculations on the optimized ground and excited state structures of both compounds were found to correlate well with the experimental findings.
UR - http://www.scopus.com/inward/record.url?scp=84938153271&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84938153271&partnerID=8YFLogxK
U2 - 10.1039/c5nj00842e
DO - 10.1039/c5nj00842e
M3 - Article
AN - SCOPUS:84938153271
SN - 1144-0546
VL - 39
SP - 6667
EP - 6676
JO - New Journal of Chemistry
JF - New Journal of Chemistry
IS - 8
ER -