7146
J. M. Nadeau, T. M. Swager / Tetrahedron 60 (2004) 7141–7146
1.09 (d, J¼7.2 Hz, 36H), 1.40 (sept, J¼7.5 Hz, 6H), 6.37–
6.38 (m, 2H), 6.70–6.73 (m, 4H), 7.16 (s, 2H); 13C NMR
(300 MHz; CDCl3) d 11.80, 18.02, 111.29, 120.83, 122.15,
122.75, 123.85, 136.65. MS (EI) exact mass calculated for
C30H50N2SSi2 [M]þ 526.3228, found 526.3205. Anal.
calculated for C30H50N2SSi2: C, 68.38; H, 9.56; N, 5.32;
S, 6.08. Found, C, 68.37; H, 9.81; N, 5.21; S, 6.22.
Acknowledgements
The authors are grateful for financial support provided by
the Army Research Office’s Tunable Optical Polymers
MURI program and for the use of resources provided by the
Institute for Soldier Nanotechnologies, also funded by the
Army Research Office.
4.1.3. 1,3-Di(1-triisopropylsilyl-3-pyrroyl)benzene (7).
Prepared as described for 3 from 1,3-dibromobenzene to
give a colorless crystalline solid (52% yield): mp 155–
References and notes
1
156 8C; H NMR (300 MHz; CDCl3) d 1.16 (d, J¼7.2 Hz,
36H), 1.51 (sept, J¼7.5 Hz; 6H), 6.67–6.69 (m, 2H), 6.83–
6.85 (m, 2H), 7.10–7.11 (m, 2H), 7.28–7.39 (m, 3H), 7.72–
7.73 (m, 1H); 13C NMR (300 MHz; CDCl3) d 11.90, 18.07,
109.04, 120.89, 122.67, 122.79, 125.26, 127.40, 128.88,
136.46. MS (ESI) exact mass calculated for C32H52N2Si2
[MþH]þ 521.3742, found 521.3724.
1. (a) In Handbook of Conducting Polymers; 2nd ed. Skotheim,
T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel
Dekker: New York, 1998. (b) Sadki, S.; Schottland, P.; Brodie,
N.; Sabouraud, G. Chem. Soc. Rev. 2000, 29, 283–293.
2. (a) Roncali, J. Chem. Rev. 1992, 92, 711–738.
(b) McCullough, R. D. Adv. Mater. 1998, 10, 93–116.
3. (a) Deronzier, A.; Moutet, J. C. Acc. Chem. Res. 1989, 22,
249–255. (b) Masuda, H.; Kaeriyama, K. Synth. Met. 1990,
38, 371–379. (c) Chen, J.; Too, C. O.; Wallace, G. G.;
Swiegers, G. F.; Skelton, B. W.; White, A. H. Electrochim.
Acta 2002, 47, 4227–4238. (d) Lee, D.; Swager, T. M. J. Am.
Chem. Soc. 2003, 125, 6870–6871. (e) Groenendaal, L.; Zotti,
G.; Aubert, P. H.; Waybright, S. M.; Reynolds, J. R. Adv.
Mater. 2003, 15, 855–879. (f) Godillot, P.; Youssoufi, H. K.;
Srivastava, P.; El Kassmi, A.; Garnier, F. Synth. Met. 1996, 83,
117–123.
4.1.4. 1,2-Di(3-pyrroyl)benzene (5). A 1.0 M solution of
TBAF in THF (1.7 mL; 1.7 mmol) was added to 3 (420 mg;
0.82 mmol) dissolved in THF. The reaction was stirred at
room temperature under argon for 15 min. The solvent was
removed under reduced pressure, and the crude product was
purified by column chromatography on silica gel (20%
hexanes in CH2Cl2) to give a colorless oil that crystallized
upon standing (132 mg; 78% yield): mp 95–96 8C; 1H
NMR (300 MHz; CDCl3) d 6.20–6.22 (m, 2H), 6.65–6.67
(m, 2H), 6.72–6.74 (m, 2H), 7.25 (dd, J¼3.3, 5.4 Hz, 2H),
7.44 (dd, J¼3.3, 5.4 Hz, 2H), 8.08 (br s, 2H); 13C NMR
(300 MHz; CDCl3) d 109.74, 116.86, 117.30, 124.99,
126.24, 130.24, 135.02. MS (ESI) exact mass calculated
for C14H12N2 [MþNa]þ 231.0893, found 231.0897.
4. Tovar, J. D.; Swager, T. M. Adv. Mater. 2001, 13, 1775–1780.
5. Tovar, J. D.; Rose, A.; Swager, T. M. J. Am. Chem. Soc. 2002,
124, 7762–7769.
6. Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell,
T. T.; Artis, D. R.; Muchowski, J. M. J. Org. Chem. 1990, 55,
6317–6328.
4.1.5. 3,4-Di(3-pyrroyl)thiophene (6). Prepared as
described for 5 from compound 4 to give a colorless oil
(50% yield): 1H NMR (300 MHz; CDCl3) d 6.28–6.31 (m,
2H), 6.73–6.77 (m, 4H), 7.18 (s, 2H), 8.18 (br s, 2H); 13C
NMR (300 MHz; CDCl3) d 109.34, 116.47, 117.58, 120.11,
121.26, 136.46. MS (ESI) exact mass calculated for
C12H10N2S [M]þ 215.0637, found 215.0646.
7. Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski,
J. M. J. Org. Chem. 1992, 57, 1653–1656.
8. Fumoto, Y.; Uno, H.; Tanaka, K.; Tanaka, M.; Murashima, T.;
Ono, N. Synthesis 2001, 3, 399–402.
9. Diaz, A. F.; Castillo, J. I.; Logan, J. A.; Lee, W. Y.
J. Electroanal. Chem. 1981, 129, 115–132.
10. Kingsborough, R. P.; Swager, T. M. Adv. Mater. 1998, 10,
1100–1104.
4.1.6. 1,3-Di(3-pyrroyl)benzene (8). Prepared as described
for 5 from compound 7 to give a colorless oil (46% yield):
1H NMR (300 MHz; CDCl3) d 6.60–6.62 (m, 2H), 6.85–
6.88 (m, 2H), 7.13–7.15 (m, 2H), 7.31–7.40 (m, 3H), 7.72–
7.73 (m, 1H), 8.28 (br s, 2H); 13C NMR (300 MHz; CDCl3)
d 106.91, 114.82, 118.99, 122.64, 122.98, 125.45, 129.07,
136.22. MS (ESI) exact mass calculated for C14H12N2 [M]þ
209.1073, found 209.1076.
11. Balasubramanian, T.; Strachan, J. P.; Boyle, P. D.; Lindsey,
J. S. J. Org. Chem. 2000, 65, 7919–7929.
12. (a) Kanazawa, K. K.; Diaz, A. F.; Geiss, R. H.; Gill, W. D.;
Kwak, J. F.; Logan, J. A.; Rabolt, J. F.; Street, G. B. J. Chem.
Soc. Chem. Commun. 1979, 854–855. (b) Diaz, A. F.; Castillo,
J. I. J. Chem. Soc. Chem. Commun. 1980, 397–398.