Paper
(E)-3-(Furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (FHPO).
RSC Advances
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Yield 90%, yellow solid, mp: 102–104 ꢃC (lit. 103–105 ꢃC), 1H
NMR (400 MHz, CDCl3): d 6.53 (dd, J ¼ 3.2 Hz, 1H), 6.77 (d, J ¼
3.6 Hz, 1H), 6.93 (d, J ¼ 16.4 Hz, 1H), 7.01 (d, J ¼ 9.2 Hz, 1H), 7.48
(d, J ¼ 10 Hz, 1H), 7.56 (t, J ¼ 15.2 Hz, 2H), 7.68 (d, J ¼ 15.2 Hz,
1H), 7.92 (d, J ¼ 10 Hz, 1H), 12.89 (s, 1H); 13C NMR (400 MHz,
CDCl3): d ¼ 113.0, 117.7, 118.9, 120.1, 129.7, 131.2, 136.4, 145.5,
151.6, 163.6, 193.4. IR (KBr), cmꢀ1: 3443 (O–H), 1641 (C]O). GC-
MS m/z: ¼ 214.22 (calcd) 215 (found).
Conclusions
Photophysical properties of FNPO, AFPO and FHPO were
studied in a series of solvents with increasing polarities.
Absorption and uorescence spectra were recorded for eighteen
different solvents and the spectral properties of FNPO, AFPO
and FHPO were calculated. Large difference of Stokes shi
values with increasing polarities for all the molecules have
indicated that the bathochromic shi of absorption and uo-
rescence spectra can be attributed to p–p* transitions. It
suggests that all the molecules were more solvated in singlet
excited state than in ground state. The singlet excited state
dipole moments were calculated using solvatochromic shi
methods and were found to be signicantly higher than that of
ground state. It conrmed that considerable charge separation
occurred between singlet excited state and ground state. This
was mainly due to ICT process associated with donor–acceptor
moiety. All the molecules were found to be more reactive due to
low band gap energy. Therefore, FNPO, AFPO and FHPO can be
considered as potential candidates for uorescent probes,
luminescent materials and optoelectronic devices.
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Acknowledgements
We wish to thank Department of IPC, IISc, Bangalore, for
providing the facility of Gaussian studies. We thank NMR
Centre, IISc, Bangalore, India, for the NMR analysis.
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