A one-step synthesis of a poly(iptycene) through an unusual Diels-Alder cyclization/dechlorination of tetrachloropentacene

Journal of the American Chemical Society

Volumn 125, Issue 34, 2003, Pages 10190-10191

  Perepichka, Dmitrii F ^a   Bendikov, Michael ^a   Meng, Hong ^a   Wudl, Fred ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLY(IPTYCENE); POLYCYCLIC AROMATIC COMPOUND; TETRACHLOROPENTACENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; CYCLOADDITION; DECHLORINATION; DIELS ALDER REACTION; GRAVIMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PYROLYSIS; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; THERMAL ANALYSIS;

EID: 0041429625     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036193i     Document Type: Article

References (17)

1. Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Wiley-VCH: New York, 1997. Geerts, Y.; Klärner, G.; Müllen, K. In Electronic Materials: The Oligomer Approach; Müllen, K., Wagner, G., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 1.
2. Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Wiley-VCH: New York, 1997. Geerts, Y.; Klärner, G.; Müllen, K. In Electronic Materials: The Oligomer Approach; Müllen, K., Wagner, G., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 1.
3. Rathore, R.; Kochi, J. K. J. Org. Chem. 1998, 63, 8630-8631.
4. (a) Shahlai, K.; Hart, H. J. Am. Chem. Soc. 1990, 112, 3687-3688.
5. (b) Hart, H. Pure Appl. Chem. 1993, 65, 27-34.
6. Long, T. M.; Swager, T. M. Adv. Mater. 2001, 13, 601-604.
7. (a) Zhu, Z.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 9670-9671.
8. (b) Swager, T. M.; Long, T. M.; Williams, V.; Yang, J.-S. Polym. Mater. Sci. Eng. 2001, 84, 304.
9. The only relevant report describes an intramolecular [4 + 2] cyclization of 1,2-bis(1,5-dichloroanthryl)ethane, where a 1,2-double bond of one anthracene moiety acts as a dienophile toward the 9,10 diene of another: Becker, H.-D.; Anderson, K. Tetrahedron Lett. 1983, 24, 3273-3276.
10. Meng, H.; Bendikov, M.; Mitchell, G.; Helgeson, R.; Wudl, F.; Bao, Z.; Siegrist, T.; Kloc, C.; Chen, C.-H. Adv. Mater. 2003, 15, 1090-1093.
11. Bao, Z. Personal communication.
12. For details, see Supporting Information.
13. 4Pn is similar to that of pentacene. See: Herwig, P. T.; Müllen, K. Adv. Mater. 1999, 11, 480-483.
14. Presumably, the ESR signal shall be attributed to the intermediate and/ or side reaction radical species.
15. 3).
16. Recently, graphitization of predefined polycyclic aromatic hydrocarbons at 800°C was reported. Gherghel, L.; Kübel, C.; Lieser, G.; Räder, H.-J.; Müllen, K. J. Am. Chem. Soc. 2002, 124, 13130-13138.
17. 4Pn (1.442 Å) is relatively long, relatively weaker, and hence more reactive.