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the Ep of the monomer 5a (Ep=0.44 V). The naphthalene derivative 5b showed an Ep of 0.55 V,
which is in between those of 5a and 9. The cyclic voltammetric data reveal that the new
monomers can be easily oxidized to their cation radicals, facilitating their electropolymerization
on an appropriate electrode surface.
Preliminary studies on the optical and electrochemical properties of the new bispyrroles reveal
that they have excellent structural and physical characteristics, which are ideal for the design of a
variety of conjugated organic materials. For example, their strong ¯uorescence and easy accessibility
for functionalization are advantageous for the design of light emitting polymers. A light emitting
polymer prepared by the Wittig±Horner±Emmons reaction of the bisformyl derivative of 5a with
the bisphosphonate ester 4a showed a strong emission at 620 nm (Èf=0.2). Detailed investigations
on the synthesis of bispyrrole based light emitting and electroactive polymers are underway.
Acknowledgements
We thank the Department of Science and Technology, Government of India, New Delhi for
®nancial support (SP/S1/G-11/97) and CSIR for a SRF to J.E.
References
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27, 7225.
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8. Zotti, G.; Zecchin, S.; Schiavon, G.; Berlin, A.; Pagani, G.; Borgonovo, M.; Lazzaroni, R. Chem. Mater. 1997, 9, 2876.
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11. Compound 5a: mp 79±80ꢀC; H NMR (300 MHz, CDCl3) ꢀ 0.87 (t, J=6.9 Hz, 6H), 1.00 (t, J=74 Hz, 6H), 1.21±
1
1.31(m, 32H), 1.54±1.59 (m, 8H), 1.78±1.83 (m, 8H), 3.98 (t, J=7.0 Hz, 4H), 4.02 (t, J=6.4 Hz, 4H), 6.15 (t,
J=3.2 Hz, 2H), 6.48 (m, 2H), 6.66 (m, 2H), 6.96 (s, 2H), 7.05 (d, J=16.4 Hz, 2H), 7.15 (d, J=16.36 Hz, 2H); 13
C
NMR (75.4 MHz, CDCl3) ꢀ 150.94, 132.13, 126.59, 122.41, 121.47, 117.81, 111.20, 108.15, 106.47, 69.12, 47.10,
31.89, 31.68, 31.57, 29.58, 29.31, 29.27, 26.08, 22.67, 19.47, 14.1, 13.93; IR (KBr) ꢁmax 2922, 2850, 1698, 1649,
1541, 1508, 1442, 1339, 1227, 1034, 958, 685; HRMS (FAB) calcd for C50H80N2O2 (M+): 740.622; found: 740.621.
Compound 5b: mp 75±77ꢀC; 1H NMR (300 MHz, CDCl3) ꢀ 0.80±0.87 (m, 12H), 1.23±1.47 (m, 40H), 1.74±1.83 (m,
8H), 3.93 (t, J=6.9 Hz, 4H), 4.04 (t, J=5.97 Hz, 4H), 6.14 (s, 2H), 6.47 (d, J=15.71 Hz, 2H), 6.42 (s, 2H), 6.62 (s,
2H), 6.85 (d, J=7.98 Hz, 2H), 7.37 (d, J=8.0 Hz, 2H), 8.0 (d, J=15.5 Hz, 2H); 13C NMR (75.4 MHz, CDCl3) ꢀ
156.56, 132.52, 132.0, 129.6, 126.26, 125.82, 121.31, 115.31, 107.83, 107.4, 105.19, 68.99, 47.02, 32.0, 31.75, 31.66,
29.70, 29.63, 29.42, 29.37, 26.93, 22.76, 19.74, 14.18, 13.8; IR (KBr) ꢁmax 2927, 2846, 1697, 1649, 1580, 1544, 1519,
1456, 1373, 1303, 1069, 1035, 950, 774, 707; HRMS (FAB) calcd C54H82N2O2 (M+): 790.6376; found: 790.6404.
Compound 9: mp 89±90ꢀC; H NMR (300 MHz, CDCl3) ꢀ 0.86 (t, J=6.7 Hz, 6H), 1.24±1.29 (m, 32H), 1.58±1.75
1
(m, 8H), 3.95 (t, J=7.1 MHz, 4H), 6.15 (t, J=2.95 Hz, 2H), 6.49 (m, 2H), 6.67 (s, 2H), 6.85 (d, J=16.0 Hz, 2H),
6.93 (d, J=16.0 Hz, 2H), 7.40 (s, 4H); 13C NMR (75.4 MHz, CDCl3) ꢀ 136.78, 131.42, 126.27, 125.62, 122.68,
116.74, 108.34,106.59, 47.14, 31.99, 31.67, 29.7, 29.6, 29.41, 29.3, 26.9, 22.76, 14.1; IR (KBr) ꢁmax 2921, 2849, 1695,
1649, 1541, 1506, 1472, 1074, 950, 689.