The ground state spin multiplicity of Schlenk-type biradicals and the influence of additional linkage to ladder type structures

Chemical Physics

Volumn 206, Issue 3, 1996, Pages 339-351

  Zhang, Jingping ^a,c   Karabunarliev, Stoyan ^b   Baumgarten, Martin ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b BURGAS FREE UNIVERSITY   (Bulgaria)

^c NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030532994     PISSN: 03010104     EISSN: None     Source Type: Journal    
DOI: 10.1016/0301-0104(96)00027-4     Document Type: Article

References (54)

1. J.S. Miller and A.J. Epstein, Chem. Rev. 88 (1988) 201; J.S. Miller and A.J. Epstein, Angew. Chem. Intern. Ed. Engl. 33 (1994) 385.
2. J.S. Miller and A.J. Epstein, Chem. Rev. 88 (1988) 201; J.S. Miller and A.J. Epstein, Angew. Chem. Intern. Ed. Engl. 33 (1994) 385.
3. H. Iwamura, Advan. Phys. Org. Chem. 26 (1990) 179.
4. M. Baumgarten and K. Müllen, Topics Current Chem. 169 (1994) 67.
5. H. Iwamura, Pure Appl. Chem. 59 (1987) 1595.
6. W. Schlenk and M. Brauns, Ber. Dtsch. Chem. Ges. 48 (1915) 661.
7. E. Wassermann, R.W. Murray, W.A. Yager, A.M. Trozzolo and G. Smolinsky, J. Am. Chem. Soc. 89 (1967) 5076.
8. K. Itoh, Chem. Phys. Letters 1 (1967) 235.
9. A. Rajca and S. Utamapanya, J. Org. Chem. 57 (1992) 1760.
10. A. Kistenmacher, M. Baumgarten, V. Enkelmann, J. Pawlik and K. Müllen, J. Org. Chem. 59 (1994) 2743.
11. K. Yoshizawa, K. Tanaka, T. Yamabe and J. Yamauchi, J. Chem. Phys. 96 (1992) 5516.
12. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
13. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
14. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
15. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
16. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
17. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
18. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
19. H.C. Longuet-Higgins, J. Chem. Phys. 18 (1950) 265; W.T. Borden and E.R. Davidson, J. Am. Chem. Soc. 99 (1977) 4587; A.A. Ovchinnikov, Theoret. Chim. Acta 47 (1978) 297; H.M. McConnell, J. Chem. Phys. 39 (1963) 1910; N. Mataga, Theoret. Chim. Acta 10 (1968) 372; D.J. Klein, J. Pure Appl. Chem. 55 (1983) 299; T.P. Radhakrishnan, Z.G. Soos, H. Endres and L.J. Azevedo, J. Chem. Phys. 85 (1986) 1126; H. Fukutome, A. Takahashi and M.A. Ozaki, Chem. Phys. Letters 133 (1987) 34.
20. P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; D. Dohnert and J. Koutecky, J. Am. Chem. Soc. 102 (1980) 1789; J. Koutecky, D. Dohnert, P.S. Wormer, J. Paldus and J. Cizek, J. Chem. Phys. 80 (1984) 2244; D.J. Klein, S.A. Alexander and M. Randic, Mol. Cryst. Liq. Cryst. 176 (1989) 109.
21. P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; D. Dohnert and J. Koutecky, J. Am. Chem. Soc. 102 (1980) 1789; J. Koutecky, D. Dohnert, P.S. Wormer, J. Paldus and J. Cizek, J. Chem. Phys. 80 (1984) 2244; D.J. Klein, S.A. Alexander and M. Randic, Mol. Cryst. Liq. Cryst. 176 (1989) 109.
22. P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; D. Dohnert and J. Koutecky, J. Am. Chem. Soc. 102 (1980) 1789; J. Koutecky, D. Dohnert, P.S. Wormer, J. Paldus and J. Cizek, J. Chem. Phys. 80 (1984) 2244; D.J. Klein, S.A. Alexander and M. Randic, Mol. Cryst. Liq. Cryst. 176 (1989) 109.
23. P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; D. Dohnert and J. Koutecky, J. Am. Chem. Soc. 102 (1980) 1789; J. Koutecky, D. Dohnert, P.S. Wormer, J. Paldus and J. Cizek, J. Chem. Phys. 80 (1984) 2244; D.J. Klein, S.A. Alexander and M. Randic, Mol. Cryst. Liq. Cryst. 176 (1989) 109.
24. E.R. Davidson, W.T. Borden and J. Smith, J. Am. Chem. Soc. 100 (1978) 3299; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 11 (1989) 3773; Y. Osamura, W.T. Borden and K. Morokuma, J. Am. Chem. Soc. 106 (984) 5112; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 108 (1986) 8086;
25. E.R. Davidson, W.T. Borden and J. Smith, J. Am. Chem. Soc. 100 (1978) 3299; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 11 (1989) 3773; Y. Osamura, W.T. Borden and K. Morokuma, J. Am. Chem. Soc. 106 (984) 5112; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 108 (1986) 8086;
26. E.R. Davidson, W.T. Borden and J. Smith, J. Am. Chem. Soc. 100 (1978) 3299; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 11 (1989) 3773; Y. Osamura, W.T. Borden and K. Morokuma, J. Am. Chem. Soc. 106 (984) 5112; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 108 (1986) 8086;
27. E.R. Davidson, W.T. Borden and J. Smith, J. Am. Chem. Soc. 100 (1978) 3299; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 11 (1989) 3773; Y. Osamura, W.T. Borden and K. Morokuma, J. Am. Chem. Soc. 106 (984) 5112; P. Du, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 108 (1986) 8086;
28. S. Kato, K. Morokuma, D. Feller, E.R. Davidson and W.T. Borden, J. Am. Chem. Soc. 105 (1983) 1791; R.C. Fort, Jr., S.J. Getty, D.A. Hrovat, P.M. Lahti and W.T. Borden. J. Am. Soc. 114 (1992) 7549.
29. S. Kato, K. Morokuma, D. Feller, E.R. Davidson and W.T. Borden, J. Am. Chem. Soc. 105 (1983) 1791; R.C. Fort, Jr., S.J. Getty, D.A. Hrovat, P.M. Lahti and W.T. Borden. J. Am. Soc. 114 (1992) 7549.
30. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
31. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
32. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
33. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
34. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
35. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
36. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
37. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
38. N. Tyutyulkov, P. Schuster and O. Polansky, Theoret. Chim. Acta 63 (1983) 291; N. Tyutyulkov, O. Polansky, P. Schuster, S. Karabunarliev and C. Ivanov, Theoret. Chim. Acta 67 (1985) 211; N. Tyutyulkov, S. Karabunarliev and S. Tsonchev, Synth. Met. 32 (1989) 51; K. Nasu, Phys. Rev. B 33 (1986) 330; K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J. 24 (1992) 857; P.M. Lahti, A.R. Rossi and J.A. Berson, J. Am. Chem. Soc. 107 (1985) 2273; P.M. Lahti, A.S. Ichimura and J.A. Berson, J. Org. Chem. 54 (1989) 958; P.M. Lahti and A.S. Ichimura, J. Org. Chem. 56 (1991) 3030; N. Tyutyulkov, S. Karabunarliev and C. Ivanov, Mol. Cryst. Liq. Cryst. 176 (1989) 139.
39. K. Yoshizawa, K. Tanaka, T. Yamabe and J. Yamauchi, J. Phys. Chem. 98 (1994) 1851.
40. K. Müllen, M. Baumgarten, N. Tyutyulkov and S. Karabunarliev, Synth. Met. 40 (1991) 127; N. Tyutyulkov, S. Karabunarliev, K. Müllen and M. Baumgarten, Synth. Met. 52 (1992) 71.
41. K. Müllen, M. Baumgarten, N. Tyutyulkov and S. Karabunarliev, Synth. Met. 40 (1991) 127; N. Tyutyulkov, S. Karabunarliev, K. Müllen and M. Baumgarten, Synth. Met. 52 (1992) 71.
42. M. Baumgarten, S. Karabunarliev, K.-H. Koch, K. Müllen and N. Tyutyulkov, Synth. Met. 47 (1992) 21; N. Tyutyulkov, S. Karabunarliev, K. Müllen and M. Baumgarten, Synth. Met. 53 (1993) 205.
43. M. Baumgarten, S. Karabunarliev, K.-H. Koch, K. Müllen and N. Tyutyulkov, Synth. Met. 47 (1992) 21; N. Tyutyulkov, S. Karabunarliev, K. Müllen and M. Baumgarten, Synth. Met. 53 (1993) 205.
44. M. Baumgarten, K. Müllen, N. Tyutyulkov and G. Madjarova, Chem. Phys. 169 (1993) 81.
45. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.J.P. Stewart, J. Am. Chem. Soc. 107 (1985) 3902.
46. M.J.S. Dewar and W. Thiel, J. Am. Chem. Soc. 99 (1977) 4899.
47. J.J.P. Stewart, J. Comput. Chem. 2 (1989) 209, 221.
48. J. Soto, V. Hernandes and J.T. Lepez Navarrete, Synth. Met. 51 (1992) 229.
49. MOPAC Version 6.0, J.J.P. Stewart and J. Frank, Seiler Research Laboratory, United States Air Force Academy, CO 80840 (1990).
50. S. Fang, M.-S. Lee, D.A. Hrovat and W.T. Borden, J. Am. Chem. Soc. 117 (1995) 6727.
51. Y. Teki, T. Takui, K. Sato, A. Yamashita, M. Okamoto, T. Kinoshita and K. Itoh, Mol. Cryst. Liq. Cryst. 232 (1993) 261.
52. K.R. Stickley and S.C. Blackstock, J. Am. Chem. Soc. 116 (1994) 11576.
53. H.G. Aurich, E. Deuschle and I. Lotz, J. Chem. Res. (S) (1977) 248.
54. A.W. Hanson, Acta Cryst. 6 (1953) 32.