RSC Advances
Page 4 of 6
The electrochemical behaviors of the triazine 3ꢀ6 were studied by
the cyclic voltammetric analysis in THF as a solvent (Figure. 4).
In summary we report the synthesis of donorꢀacceptor type
ferrocenyl substituted 1,3,5ꢀtriazine by Sonogshira coupling
The triazine 3ꢀ6 exhibits one reversible reduction wave, and one 35 reaction via conventional and microwave method. The
oxidation wave corresponding to 1,3,5ꢀtriazine, and ferrocene
moiety respectively. The cyclic voltammograms of triazines 3ꢀ6
are shown in supporting information. The oxidation potential of
triazine lie in the range of 0.60 to 0.69 V (Table 1). The oxidation
photophysical, and electrochemical studies show strong
electronic communication between the donor, and acceptor units.
The triazine 3ꢀ6 are thermally and photophysically stable. The
crystal structure of 3 exhibits interesting layer pattern structures.
5
0
5
potential data of triazine 3ꢀ6 reveals that the oxidation of the 40 The studies towards the use of these triazines multiꢀphoton
ferrocene unit in the triazines becomes difficult compared to free
ferrocene, which indicates that the electron density of the
ferrocenyl moiety is delocalized into the triazine unit. The
compound 3 show hardest oxidation compare to rest of the
absorbing materials are presently being carried out in our
laboratory.
1
Acknowledgements
triazines, which indicates maximum strong electronic 45 The work was supported by DST, and CSIR Govt. of India, New
communication in triazine 3. The oxidation potential of the
triazines following the order 3 > 4 > 5 > 6. The reduction
potential of the triazines are not much affected by the donor
group as the reduction potential data show small difference.
Delhi. We gratefully acknowledge Sophisticated Instrumentation
Centre (SIC), IIT Indore.
1
Notes and References
Corresponding Author
5
5
0
5
*Department of Chemistry
Indian Institute of Technology Indore, Indoreꢀ 452 017, India
Corresponding author. Tel.: +91 731 2438710; fax: +91 731 2361482,
Email: rajneeshmisra@iiti.ac.in
-
-
-
-
5
5
5
5
4
3
2
1
.0x10
.0x10
.0x10
.0x10
20
-
3
Electronic Electronic Supplementary Information (ESI) available:
1
13
[
General experimental methods, and copies of H NMR, C NMR and
0
.0
HRMS spectra, and Cyclic viltammogarams , TGA graphs of all new
compounds, crystallographic information file (CIF) and crytal refinement
data for compound 3. see DOI:
-
5
-
1.0x10
1
.0
0.5
0.0
-0.5
-1.0
-1.5
Potential vs Ag/AgCl
60
25
1
(a) S. I. Kato, M. Kivala, W. B. schweizer, C. Boudon, J. P.
Gisselbrecht, F. Diederich, Chem. Eur. J. 2009, 15, 8687ꢀ8691.
(b) M. Jordan, M. Kivala, C. Boudon, J. P. Gisselbrecht, W.
B. Schweize, P. Seiler, F. Diederich, Chem. Asian J. 2011, 6,
Fig. 4 Cyclic voltammogram of compound 3 in 0.1 M solution of
Bu4NPF6 in THF (1.0 × 10−4 M) at 100 mV S−1 scan rate
6
7
7
8
5
0
5
0
Table 1. Photophysicaland electrochemicaldata for triazine 3ꢀ6
3
96ꢀ401.
a)M. Pierre, M. A. Beaujuge, R. J. Reynolds, Acc. Chem. Res.
010, 43, 1396ꢀ1407. b) P. D. Hoog, P. Gamez, W. L. Driessen, J.
b
−1
−1
Compound
λ
max (nm)
ε (M cm )
E
oxid (V)
E
red (V)
2
3
2
3
267
0.69
ꢀ 0.91
ꢀ 0.95
Reedijk, Tetrahedron Lett. 2002, 43, 6783ꢀ6786.
3
4
33
79
6916
M. Thelakkat, R. Fink, P. Posch, J. Ring, H. W. Schmidt,
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4
5
257
0.67
0.67
39ꢀ395.
2
79
ꢀ
11416
4
5
6
R. Fink, Y. Heischkel, M. Thelakkat, H. W. Schmidt, C. Jonda,
M. Huppauff, Chem. Mater. 1998, 10, 3620ꢀ3622.
283
ꢀ0.95
R. Fink, C. Fenz, M. Thelakkat, H. W. Schmidt,
3
4
49
68
18083
15500
Macromolecules 1997, 30, 8177ꢀ8181.
a) C. H. Lee, T. Yamamoto, Bull. Chem. Soc. Jpn. 2002, 75, 615ꢀ618.
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c) P. Gamez, P. D. Hoog, O. Roubeau, M. Lutz, W. L. Driessen, A.
L. Spek, J. Reedijk, Chem. Commun. 2002, 1488ꢀ1489.
d) P. Gamez, P. D. Hoog, M. Lutz, W. L. Driessen, A. L. Spek, J.
Reedijk, Polyhedron 2003, 20, 205ꢀ210.
6
286
3
0.60
0.58
ꢀ0.93
ꢀ
40
ꢀ
Ferrocene
–
–
b
30
The absorption cofficient (ε) values belongs to absorption maxima
e) P. D. Hoog, P. Gamez, O. Roubeau, M. Lutz, W. L. Driessen, A.
L. Spek, J. Reedijk, New J. Chem. 2003, 27, 18–21.
(λ
max (nm) of triazine 3ꢀ6)
4
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