The hypothetical polymer obtained by linear annelation of benzene units, polyacene (PAC) (C4H2)n, has received considerable attention over the last 50 years. This interest is due to the unusual electronic structure that is assumed to result in usual physical properties. The review summarizes the theoretical investigations of PAC research. The most recent computational analyses available in the literature are based on density functional theory (DFT) for PAC and on the complete active space self-consistent field (CASSCF) method for oligoacenes and suggest an undistorted symmetrical structure with an antiferromagnetic (AFM) coupling of electrons.
Conference
International Symposium on Novel Aromatic Compounds (ISNA-13), International Symposium on Novel Aromatic Compounds, ISNA, Novel Aromatic Compounds, 13th, Luxembourg City, Luxembourg, 2009-07-19–2009-07-24
References
1 10.1002/cber.19300631109, E. Clar, F. John. Ber. Dtsch. Chem. Ges. B63, 2967 (1930).Search in Google Scholar
2a 10.1002/cber.19390721002, E. Clar. Ber. Dtsch. Chem. Ges. B72, 1817 (1939).Search in Google Scholar
2b C. Marschalk. Bull. Soc. Chim.6, 1112 (1939).Search in Google Scholar
3 E. Clar. Chem. Ber.75, 1330 (1942).10.1002/cber.19420751114Search in Google Scholar
4 10.1021/ja01609a055, W. J. Bailey, C.-W. Liao. J. Am. Chem. Soc.77, 992 (1955).Search in Google Scholar
5 C. Marschalk. Bull. Soc. Chim.10, 511 (1943).Search in Google Scholar
6 10.1039/jr9570002681, B. Boggiano, E. Clar. J. Chem. Soc. 2681 (1957).Search in Google Scholar
7 10.1021/ja063823i, R. Mondal, B. K. Shah, D. C. Neckers. J. Am. Chem. Soc.128, 9612 (2006).Search in Google Scholar
8 E. Clar. Polycyclic Hydrocarbons, Academic Press, London (1964).10.1007/978-3-662-01668-8Search in Google Scholar
9 10.1002/anie200906355, C. Tönshoff, H. F. Bettinger. Angew. Chem., Int. Ed. (2010).Search in Google Scholar
10 L. Salem, H. C. Longuet-Higgins. Proc. R. Soc. London A255, 435 (1960).Search in Google Scholar
11 10.1021/cr030666m, M. Bendikov, F. Wudl, D. F. Perepichka. Chem. Rev.104, 4891 (2004).Search in Google Scholar
12 10.1002/1521-3773(20010316)40:6<1037::AID-ANIE10370>3.0.CO;2-H, F. Würthner. Angew. Chem., Int. Ed.40, 1037 (2001).Search in Google Scholar
13 10.1002/cphc.200600078, F. Würthner, R. Schmidt. ChemPhysChem7, 793 (2006).Search in Google Scholar
14 10.1021/cr050966z, J. E. Anthony. Chem. Rev.106, 5028 (2006).Search in Google Scholar
15 10.1002/anie.200604045, J. E. Anthony. Angew. Chem., Int. Ed.47, 452 (2008).Search in Google Scholar
16a 10.1021/ja048919w, M. Bendikov, H. M. Duong, K. Starkey, K. N. Houk, E. A. Carter, F. Wudl. J. Am. Chem. Soc.126, 7416 (2004).Search in Google Scholar
16b 10.1021/ja045878v, Erratum: M. Bendikov, H. M. Duong, K. Starkey, K. N. Houk, E. A. Carter, F. Wudl. J. Am. Chem. Soc.126, 10493 (2004).Search in Google Scholar
17 H. C. Longuet-Higgins, L. Salem. Proc. R. Soc. London A251, 172 (1959).Search in Google Scholar
18 E. V. Anslyn, D. A. Dougherty. Modern Physical Organic Chemistry, University Science Books, Sausalito, CA (2006).Search in Google Scholar
19 R. Hoffmann. Solids and Surfaces: A Chemist’s View of Bonding in Extended Structures, Wiley-VCH, New York (1988).Search in Google Scholar
20 R. Peierls. Quantum Theory of Solids, Oxford University Press, London (1955).Search in Google Scholar
21 10.1103/PhysRevB.28.7236, S. Kivelson, O. L. Chapman. Phys. Rev. B28, 7236 (1983).Search in Google Scholar
22 10.1007/BF00530207, M. R. Boon. Theor. Chim. Acta (Berl.)23, 109 (1971).Search in Google Scholar
23 M.-H. Whangbo, R. Hoffmann, R. B. Woodward. Proc. R. Soc. London A366, 23 (1979).Search in Google Scholar
24 10.1021/j100283a004, J. P. Lowe, S. A. Kafafi, J. P. LaFemina. J. Phys. Chem.90, 6602 (1986).Search in Google Scholar
25 10.1016/0038-1098(83)90617-8, M. Kertesz, R. Hoffmann. Solid State Commun.47, 97 (1983).Search in Google Scholar
26 N. N. Tyutyulkov, O. E. Polansky, J. Fabian. Z. Naturforsch., A: Phys. Sci.30, 1308 (1975).Search in Google Scholar
27 10.1063/1.443405, J. L. Brédas, R. R. Chance, R. H. Baughman, R. Silbey. J. Chem. Phys.76, 3673 (1982).Search in Google Scholar
28 10.1021/ja00248a004, J. Kao, A. C. Lilly. J. Am. Chem. Soc.109, 4149 (1987).Search in Google Scholar
29 10.1016/0022-3697(83)90089-6, K. Tanaka, K. Ohzeki, S. Nankai, T. Yamabe, H. Shirakawa. J. Phys. Chem. Solids44, 1069 (1983).Search in Google Scholar
30 10.1002/qua.560350207, M. Kertesz, Y. S. Lee, J. J. P. Stewart. Int. J. Quant. Chem.35, 305 (1989).Search in Google Scholar
31 10.1021/j100181a031, J. Chandrasekhar, P. K. Das. J. Phys. Chem.96, 679 (1992).Search in Google Scholar
32 10.1103/PhysRevB.57.8927, B. Srinivasan, S. Ramasesha. Phys. Rev. B57, 8927 (1998).Search in Google Scholar
33 10.1103/PhysRevB.65.155204, C. Raghu, Y. A. Pati, S. Ramasesha. Phys. Rev. B65, 155204 (2002).Search in Google Scholar
34 10.1103/PhysRevA.71.022508, T. A. Niehaus, M. Rohlfing, F. Della Sala, A. Di Carlo, T. Frauenheim. Phys. Rev. A71, 022508 (2005).Search in Google Scholar
35 10.1063/1.464641, J. Cioslowski. J. Chem. Phys.98, 473 (1993).Search in Google Scholar
36 10.1021/jp003678+, G. Madjarova, T. Yamabe. J. Phys. Chem. B105, 2534 (2001).Search in Google Scholar
37 10.1021/jo010391f, K. N. Houk, P. S. Lee, M. Nendel. J. Org. Chem.66, 5517 (2001).Search in Google Scholar PubMed
38 10.1103/PhysRevB.32.8136, I. Bozovic. Phys. Rev. B32, 8136 (1985).Search in Google Scholar
39 10.1063/1.434318, R. Seeger, J. A. Pople. J. Chem. Phys.66, 3045 (1977).Search in Google Scholar
40 10.1002/(SICI)1096-987X(20000430)21:6<483::AID-JCC7>3.0.CO;2-O, D. Dehareng, G. Dive. J. Comput. Chem.21, 483 (2000).Search in Google Scholar
41 10.1063/1.471637, R. Bauernschmitt, R. Ahlrichs. J. Chem. Phys.104, 9047 (1996).Search in Google Scholar
42 10.1063/1.1674065, J. Čížek, J. Paldus. J. Chem. Phys.53, 821 (1970).Search in Google Scholar
43 10.1021/ja00240a053, S. D. Kahn, W. J. Hehre, J. A. Pople. J. Am. Chem. Soc.109, 1871 (1987).Search in Google Scholar
44 10.1143/PTP.40.998, H. Fukutome. Prog. Theor. Phys.40, 998 (1968).Search in Google Scholar
45 10.1016/0375-9601(83)90835-6, M. Baldo, G. Piccitto, R. Pucci, P. Tomasello. Phys. Lett. A95, 201 (1983).Search in Google Scholar
46 10.1007/BF00754218, M. M. Mestechkin, G. E. Vaiman, A. L. Vul’fov. J. Struct. Chem.25, 164 (1985).Search in Google Scholar
47 10.1063/1.451017, M. Kimura, H. Kawabe, K. Nishikawa, S. Aono. J. Chem. Phys.85, 3090 (1986).Search in Google Scholar
48 10.1088/0022-3719/21/5/003, M. P. O’Connor, R. J. Watts-Tobin. J. Phys. C: Solid State Phys.21, 825 (1988).Search in Google Scholar
49 10.1016/0009-2614(82)83589-6, H. Angliker, E. Rommel, J. Wirz. Chem. Phys. Lett.87, 208 (1982).Search in Google Scholar
50 10.1063/1.2768362, J. Hachmann, J. J. Dorando, M. Avilés, G. K.-L. Chan. J. Chem. Phys.127, 134309 (2007).Search in Google Scholar PubMed
51 10.1021/jp0765087, D. Jiang, S. Dai. J. Phys. Chem. A112, 332 (2008).Search in Google Scholar PubMed
52 10.1021/jp9015728, Z. Qu, D. Zhang, C. Liu, Y. Jiang. J. Phys. Chem. A113, 7909 (2009).Search in Google Scholar PubMed
53 10.1103/PhysRevB.74.045426, M. C. dos Santos. Phys. Rev. B74, 045426 (2006).Search in Google Scholar
54 10.1002/cber.19150480189, W. Schlenk, M. Brauns. Ber. Dtsch. Chem. Ges.48, 661 (1915).Search in Google Scholar
55 10.1021/ja9095472, A persistent, highly substituted nonacene was recently reported: I. Kaur, M. Jazdzyk, N. N. Stein, P. Prusevich, G. P. Miller. J. Am. Chem. Soc.132, 1261 (2010).Search in Google Scholar PubMed
© 2013 Walter de Gruyter GmbH, Berlin/Boston
