Stuctural Reorganization of Anthracene-Bridged Stilbenoids by Oxidation and Reduction

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 24, 1997, Pages 2817-2819

  Knorr, Andreas ^a   Daub, Jörg ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Arenes; Cyclic voltammetry; Electron transfer; Radical ions; Stilbenes

Indexed keywords

EID: 0032491785     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199728171     Document Type: Article

References (19)

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2. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim 1995; H. Meier, Angew. Chem. 1992, 104, 1425; Angew. Chem. Int. Ed. Engl. 1992, 31, 199.
3. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim 1995; H. Meier, Angew. Chem. 1992, 104, 1425; Angew. Chem. Int. Ed. Engl. 1992, 31, 199.
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5. A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664; J. Daub, M. Beck, A. Knorr, H. Spreitzer, Pure Appl. Chem. 1996, 68, 1399; K. Kelnhofer, A. Knorr, J. Daub, Y.-H. Tak, H. Bässler, Acta Polym. 1997, 48, 188.
6. A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664; J. Daub, M. Beck, A. Knorr, H. Spreitzer, Pure Appl. Chem. 1996, 68, 1399; K. Kelnhofer, A. Knorr, J. Daub, Y.-H. Tak, H. Bässler, Acta Polym. 1997, 48, 188.
7. A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664; J. Daub, M. Beck, A. Knorr, H. Spreitzer, Pure Appl. Chem. 1996, 68, 1399; K. Kelnhofer, A. Knorr, J. Daub, Y.-H. Tak, H. Bässler, Acta Polym. 1997, 48, 188.
8. A. Knorr, Dissertation, Universität Regensburg, 1995; F. Effenberger, C.-P. Niesert, Synthesis 1992, 1137; G. Bartocci, U. Mazzucato, A. Spalletti, G. Orlandi, G. Poggi, J. Chem Soc. Faraday Trans. 1992, 3139; T. Arai, T. Karatsu, H. Misawa, Y. Kuriyama. H. Okamoto, T. Hiresaki, H. Furuuchi, H. Zeng, H. Sakuragi, K. Tokumaru, Pure Appl. Chem. 1988, 60, 989.
9. A. Knorr, Dissertation, Universität Regensburg, 1995; F. Effenberger, C.-P. Niesert, Synthesis 1992, 1137; G. Bartocci, U. Mazzucato, A. Spalletti, G. Orlandi, G. Poggi, J. Chem Soc. Faraday Trans. 1992, 3139; T. Arai, T. Karatsu, H. Misawa, Y. Kuriyama. H. Okamoto, T. Hiresaki, H. Furuuchi, H. Zeng, H. Sakuragi, K. Tokumaru, Pure Appl. Chem. 1988, 60, 989.
10. A. Knorr, Dissertation, Universität Regensburg, 1995; F. Effenberger, C.-P. Niesert, Synthesis 1992, 1137; G. Bartocci, U. Mazzucato, A. Spalletti, G. Orlandi, G. Poggi, J. Chem Soc. Faraday Trans. 1992, 3139; T. Arai, T. Karatsu, H. Misawa, Y. Kuriyama. H. Okamoto, T. Hiresaki, H. Furuuchi, H. Zeng, H. Sakuragi, K. Tokumaru, Pure Appl. Chem. 1988, 60, 989.
11. A. Knorr, Dissertation, Universität Regensburg, 1995; F. Effenberger, C.-P. Niesert, Synthesis 1992, 1137; G. Bartocci, U. Mazzucato, A. Spalletti, G. Orlandi, G. Poggi, J. Chem Soc. Faraday Trans. 1992, 3139; T. Arai, T. Karatsu, H. Misawa, Y. Kuriyama. H. Okamoto, T. Hiresaki, H. Furuuchi, H. Zeng, H. Sakuragi, K. Tokumaru, Pure Appl. Chem. 1988, 60, 989.
12. 2/hexanes.
13. a) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; b) PM3: J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209; c) G. Rauhut, A. Alex, J. Chandrasekhar, T. Steinke, T. Clark, VAMP5.01, Oxford Molecular Ltd., Oxford, 1993. d) The geometries of closed-shell species were optimized using the RHF formalism, and those of open-shell species were treated with the AUHF formalism. All obtained structures were characterized as stationary points on the energy surface by vibrational analysis.
14. a) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; b) PM3: J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209; c) G. Rauhut, A. Alex, J. Chandrasekhar, T. Steinke, T. Clark, VAMP5.01, Oxford Molecular Ltd., Oxford, 1993. d) The geometries of closed-shell species were optimized using the RHF formalism, and those of open-shell species were treated with the AUHF formalism. All obtained structures were characterized as stationary points on the energy surface by vibrational analysis.
15. a) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; b) PM3: J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209; c) G. Rauhut, A. Alex, J. Chandrasekhar, T. Steinke, T. Clark, VAMP5.01, Oxford Molecular Ltd., Oxford, 1993. d) The geometries of closed-shell species were optimized using the RHF formalism, and those of open-shell species were treated with the AUHF formalism. All obtained structures were characterized as stationary points on the energy surface by vibrational analysis.
16. a) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902; b) PM3: J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209; c) G. Rauhut, A. Alex, J. Chandrasekhar, T. Steinke, T. Clark, VAMP5.01, Oxford Molecular Ltd., Oxford, 1993. d) The geometries of closed-shell species were optimized using the RHF formalism, and those of open-shell species were treated with the AUHF formalism. All obtained structures were characterized as stationary points on the energy surface by vibrational analysis.
17. -1, again depending on the compound and the semiempirical method applied. It is remarkable that rotation about bond d2 (a formal single bond) leads to such high energy barriers. Furthermore, according to the semiempirical calculations the s-cis conformation of these doubly charged species represents a transition state and not a minimum on the energy surface of the rotation process (all transition states were characterized by vibrational analysis).
18. H. Spreitzer, M. Scholz, G. Gescheidt, J. Daub, Liebigs Ann. 1996, 2069.
19. 2- in the calculation of the UV transitions yields numbers that significantly deviate from the experimental findings. For computational details, see ref. [5c].