4
Tetrahedron Letters
16. Ooyama, Y.; Shimada, Y.; Inoue, S.; Nagano, T.; Fujikawa, Y.;
The calculated electron life time values were listed in the Table
Komaguchi, K.; Imae I.; Harima, Y. New J. Chem. 2011, 35, 111–
118.
2. In the case of Ar-ma sensitized DSSC, maximum electron
lifetime of 14.40 ms was achieved while comparing with the
other sensitizers based DSSC. This indicates that the Ar-ma
based DSSC shows more effective suppression of injected
electrons recombination with the I3– in the electrolyte which leads
to the enhancement in the photo voltage, photocurrent and the
device efficiency.
17. Hagberg, D. P.; Edvinsson, T.; Marinado, T.; Boschloo, G.;
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21. Wu, T. Y.; Tsao, M. H.; Chen, F. L.; Su, S. G.; Chang, C. W.;
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In this study, all dyes were synthesized through one-pot
Knoevenagel condensation reaction. The photophysical,
electrochemical and photovoltaic properties of synthesized metal-
free organic dyes containing diphenylamine and diethylamine
donor which is linked to the acrylic acid and rhodanine-3-acetic
acid acceptor through a phenyl spacer was performed. Due to
the better binding nature, the acrylic acid acceptor dye (Ar-ma)
shows higher efficiency compared to the same dye having cyano
acrylic acid as acceptor instead of acrylic acid. In general, acrylic
acid acceptor based dyes shows higher DSSC performance
compared to the rhodanine-3-acetic acid acceptor based dyes.
From the experimental and theoretical results, we conclude that
the anchoring group must be in conjugation with the entire dye
molecule. In addition, the spacer should be essentially
coplanar with acceptor group to (i) make more cathodic shift in
oxidation potential, (ii) reduces the electron recombination at the
TiO2/dye/electrolyte interface and (iii) enhance the electron life
time on the TiO2 conduction band.
22. (E)-3-(4-(diethylamino)phenyl)acrylic acid (Al-ma): 1 g (5.64
mmol, 1eq) of 4-diethyl amino benzaldehyde and 0.881 g (8.46
mmol, 1.5 eq) of malonic acid were added to 25 mL of acetonitrile
and the solution was refluxed for 7 hrs in the presence of
piperidine 3.4 ml (33.84 mmol, 6 eq). After cooling to room
temperature, the mixture was poured into ice water. The
precipitate was filtered and washed with distilled water. After
drying under vacuum, the precipitate was purified by
recrystallization from ethanol to afford pure brown crystals (yield:
1.04 g; 84 %). M.p=180-182 oC. 1H NMR (CDCl3, ppm):
d, 1H, J=15.5 Hz7.44 (d, 2H, J=8.5 Hz), 6.66 (d, 2H, J=8
Hz), 6.21 (d, 1H, J=15.5 Hz), 3.44-3.40 (q, 4H, J=7Hz), 1.21 (t,
6H, J=7Hz). 13C NMR (DMSO-d6, ppm): 173.49, 154.17,
149.92, 135.29, 125.88, 117.42, 116.31, 48.97, 17.63. IR (KBr
pellet, cm-1): 3444, 3034, 2967, 1666, 1591, 1434, 1355, 1185,
978, 826. Anal. Calcd for C13H17NO2: C, 71.21; H, 7.81; N, 6.39.
Found: C, 71.1; H, 7.76; N, 6.35. LC-MS Anal. Calcd. for
C13H17NO2: 219.13. Found: 220.1 [M+H]+. Refer supporting
information for other synthetic procedures.
23. Chen, Y.; Li, C.; Zeng, Z.; Wang, W.; Wang, X.; Zhang, B. Chem.
Lett. 2005, 34, 762-763.
24. Yanga, C. H.; Linb, W. C.; Wanga, T. L.; Shieha, Y. T.; Chena,
W. J.; Liaoa, S. H.; Suna, Y. K. Mater. Chem. Phys. 2011, 130,
635– 643.
25. Roquet, S.; Cravino, A.; Leriche, P.; Aleveque, O.; Frere, P.;
Roncali, J. J. Am. Chem. Soc. 2006, 128, 3459-3466.
26. Yang, C. H.; Chen, H. L.; Chuang, Y. Y.; Wu, C. G.; Chen, C. P.;
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27. Chang, Y. J.; Chow, T. J. Tetrahedron 2009, 65, 4726–4734.
28. Zhang, G.; Bai, Y.; Li, R.; Shi, D.; Wenger, S.; Zakeeruddin, S.
M.; Gratzel, M.; Wang, P. Energy Environ Sci. 2009, 2, 92–95.
29. Zhang, G.; Bala, H.; Cheng, Y.; Shi, D.; Lv, X.; Yu, Q.; Wang, P.
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Acknowledgments:
Authors thank DST, New Delhi (Ref. No.SR/S1/PC-
49/2009) and DST-FIST, New Delhi (SR/FT/CSI-190/2008 dated
16th Mar 2008) for the sanction of research fund towards
development of new facilities. Author S. Manoharan thanks
UGC, New Delhi for a junior research fellowship. The author SA
thanks Department of Science & Technology for the India-Spain
collaborative research grant (DST/INT/Spain/P-37/11 dt.16th Dec
2011) to him.
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