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Volumn , Issue 1, 1998, Pages 81-89

The synthesis and spectroscopic properties of a [2]catenane incorporating an anthracene chromophoric unit

Author keywords

Catenanes; Chromophoric units; Crown compounds; Cyclobis(paraquat p phenylene)

Indexed keywords


EID: 0342744438     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199801)1998:1<81::AID-EJOC81>3.0.CO;2-P     Document Type: Article
Times cited : (11)

References (56)
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    • Bouas-Laurent, H.1    Castellan, A.2    Daney, M.3    Desvergne, J.-P.4    Guinand, G.5    Marsau, P.6    Riffaud, M.-H.7
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    • Guinand, G.1    Marsau, P.2    Bouas-Laurent, H.3    Castellan, A.4    Desvergne, J.-P.5    Lamotte, M.6
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    • Prodi, L.1    Ballardini, R.2    Gandolfi, M.T.3    Balzani, V.4    Desvergne, J.-P.5    Bouas-Laurent, H.6
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    • For references regarding the incorporation of anthracene derived subunits into supramolecular systems, see: [7a] A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218, and references cited therein; - [7b] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317; - [7c] G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Cryst. 1987, C43, 857-860; - [7d] L. Prodi, R. Ballardini, M. T. Gandolfi, V. Balzani, J.-P. Desvergne, H. Bouas-Laurent, J. Phys. Chem. 1991, 95, 2080-2083; - [7e] I. Willner, J. Rosengaus, Y. Eichen, New. J. Chem. 1991, 15, 55-64; - [7f] F. Effenberger, G. Gotz, P. Bauerle, Chem. Ber. 1992, 125, 941-950; - [7g] H. Hopf, R. Uttermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517; - [7h] A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature (London) 1993, 364, 42-44; - [7i] F. Fages, J.-P. Desvergne, K. Kampke, H. Bouas-Laurent, J.-M. Lehn, M. Meyer, A.-M. Albrecht-Gary, J. Am Chem. Soc. 1993, 115, 3658-3664; - [7j] L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza, T. Torres, J. Org. Chem. 1993, 58, 2009-2012; - [7k] M. Jorgensen, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larssen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993, 58, 2785-2790; - [7l] D. Marquis, J.-P. Desvergne, H. BouasLaurent, J. Org. Chem. 1995, 60, 7984-7996, and references cited therein; - [7m] E. C Constable, D. R. Smith, Tetrahedron 1996, 52, 935-940; - [7n] P. Belser, R. Dux, M. Baak, L. De Cola, V. Balzani, Angew. Chem. Int. Ed. Engl. 1995, 34, 595-598; - [7o] B. Henze, D. Marquis, P. Marsau, M. Cotrait, J.-P. Desvergne, Tetrahedron Lett. 1996, 31, 5499-5502.
    • (1993) J. Am Chem. Soc. , vol.115 , pp. 3658-3664
    • Fages, F.1    Desvergne, J.-P.2    Kampke, K.3    Bouas-Laurent, H.4    Lehn, J.-M.5    Meyer, M.6    Albrecht-Gary, A.-M.7
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    • For references regarding the incorporation of anthracene derived subunits into supramolecular systems, see: [7a] A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218, and references cited therein; - [7b] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317; - [7c] G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Cryst. 1987, C43, 857-860; - [7d] L. Prodi, R. Ballardini, M. T. Gandolfi, V. Balzani, J.-P. Desvergne, H. Bouas-Laurent, J. Phys. Chem. 1991, 95, 2080-2083; - [7e] I. Willner, J. Rosengaus, Y. Eichen, New. J. Chem. 1991, 15, 55-64; - [7f] F. Effenberger, G. Gotz, P. Bauerle, Chem. Ber. 1992, 125, 941-950; - [7g] H. Hopf, R. Uttermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517; - [7h] A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature (London) 1993, 364, 42-44; - [7i] F. Fages, J.-P. Desvergne, K. Kampke, H. Bouas-Laurent, J.-M. Lehn, M. Meyer, A.-M. Albrecht-Gary, J. Am Chem. Soc. 1993, 115, 3658-3664; - [7j] L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza, T. Torres, J. Org. Chem. 1993, 58, 2009-2012; - [7k] M. Jorgensen, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larssen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993, 58, 2785-2790; - [7l] D. Marquis, J.-P. Desvergne, H. BouasLaurent, J. Org. Chem. 1995, 60, 7984-7996, and references cited therein; - [7m] E. C Constable, D. R. Smith, Tetrahedron 1996, 52, 935-940; - [7n] P. Belser, R. Dux, M. Baak, L. De Cola, V. Balzani, Angew. Chem. Int. Ed. Engl. 1995, 34, 595-598; - [7o] B. Henze, D. Marquis, P. Marsau, M. Cotrait, J.-P. Desvergne, Tetrahedron Lett. 1996, 31, 5499-5502.
    • (1993) J. Org. Chem. , vol.58 , pp. 2009-2012
    • Echegoyen, L.1    Hafez, Y.2    Lawson, R.C.3    De Mendoza, J.4    Torres, T.5
  • 23
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    • For references regarding the incorporation of anthracene derived subunits into supramolecular systems, see: [7a] A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218, and references cited therein; - [7b] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317; - [7c] G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Cryst. 1987, C43, 857-860; - [7d] L. Prodi, R. Ballardini, M. T. Gandolfi, V. Balzani, J.-P. Desvergne, H. Bouas-Laurent, J. Phys. Chem. 1991, 95, 2080-2083; - [7e] I. Willner, J. Rosengaus, Y. Eichen, New. J. Chem. 1991, 15, 55-64; - [7f] F. Effenberger, G. Gotz, P. Bauerle, Chem. Ber. 1992, 125, 941-950; - [7g] H. Hopf, R. Uttermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517; - [7h] A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature (London) 1993, 364, 42-44; - [7i] F. Fages, J.-P. Desvergne, K. Kampke, H. Bouas-Laurent, J.-M. Lehn, M. Meyer, A.-M. Albrecht-Gary, J. Am Chem. Soc. 1993, 115, 3658-3664; - [7j] L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza, T. Torres, J. Org. Chem. 1993, 58, 2009-2012; - [7k] M. Jorgensen, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larssen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993, 58, 2785-2790; - [7l] D. Marquis, J.-P. Desvergne, H. BouasLaurent, J. Org. Chem. 1995, 60, 7984-7996, and references cited therein; - [7m] E. C Constable, D. R. Smith, Tetrahedron 1996, 52, 935-940; - [7n] P. Belser, R. Dux, M. Baak, L. De Cola, V. Balzani, Angew. Chem. Int. Ed. Engl. 1995, 34, 595-598; - [7o] B. Henze, D. Marquis, P. Marsau, M. Cotrait, J.-P. Desvergne, Tetrahedron Lett. 1996, 31, 5499-5502.
    • (1993) J. Org. Chem. , vol.58 , pp. 2785-2790
    • Jorgensen, M.1    Lerstrup, K.2    Frederiksen, P.3    Bjornholm, T.4    Sommer-Larssen, P.5    Schaumburg, K.6    Brunfeldt, K.7    Bechgaard, K.8
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    • and references cited therein
    • For references regarding the incorporation of anthracene derived subunits into supramolecular systems, see: [7a] A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218, and references cited therein; - [7b] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317; - [7c] G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Cryst. 1987, C43, 857-860; - [7d] L. Prodi, R. Ballardini, M. T. Gandolfi, V. Balzani, J.-P. Desvergne, H. Bouas-Laurent, J. Phys. Chem. 1991, 95, 2080-2083; - [7e] I. Willner, J. Rosengaus, Y. Eichen, New. J. Chem. 1991, 15, 55-64; - [7f] F. Effenberger, G. Gotz, P. Bauerle, Chem. Ber. 1992, 125, 941-950; - [7g] H. Hopf, R. Uttermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517; - [7h] A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature (London) 1993, 364, 42-44; - [7i] F. Fages, J.-P. Desvergne, K. Kampke, H. Bouas-Laurent, J.-M. Lehn, M. Meyer, A.-M. Albrecht-Gary, J. Am Chem. Soc. 1993, 115, 3658-3664; - [7j] L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza, T. Torres, J. Org. Chem. 1993, 58, 2009-2012; - [7k] M. Jorgensen, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larssen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993, 58, 2785-2790; - [7l] D. Marquis, J.-P. Desvergne, H. BouasLaurent, J. Org. Chem. 1995, 60, 7984-7996, and references cited therein; - [7m] E. C Constable, D. R. Smith, Tetrahedron 1996, 52, 935-940; - [7n] P. Belser, R. Dux, M. Baak, L. De Cola, V. Balzani, Angew. Chem. Int. Ed. Engl. 1995, 34, 595-598; - [7o] B. Henze, D. Marquis, P. Marsau, M. Cotrait, J.-P. Desvergne, Tetrahedron Lett. 1996, 31, 5499-5502.
    • (1995) J. Org. Chem. , vol.60 , pp. 7984-7996
    • Marquis, D.1    Desvergne, J.-P.2    Bouaslaurent, H.3
  • 25
    • 0030041020 scopus 로고    scopus 로고
    • For references regarding the incorporation of anthracene derived subunits into supramolecular systems, see: [7a] A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218, and references cited therein; - [7b] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317; - [7c] G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Cryst. 1987, C43, 857-860; - [7d] L. Prodi, R. Ballardini, M. T. Gandolfi, V. Balzani, J.-P. Desvergne, H. Bouas-Laurent, J. Phys. Chem. 1991, 95, 2080-2083; - [7e] I. Willner, J. Rosengaus, Y. Eichen, New. J. Chem. 1991, 15, 55-64; - [7f] F. Effenberger, G. Gotz, P. Bauerle, Chem. Ber. 1992, 125, 941-950; - [7g] H. Hopf, R. Uttermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517; - [7h] A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature (London) 1993, 364, 42-44; - [7i] F. Fages, J.-P. Desvergne, K. Kampke, H. Bouas-Laurent, J.-M. Lehn, M. Meyer, A.-M. Albrecht-Gary, J. Am Chem. Soc. 1993, 115, 3658-3664; - [7j] L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza, T. Torres, J. Org. Chem. 1993, 58, 2009-2012; - [7k] M. Jorgensen, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larssen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993, 58, 2785-2790; - [7l] D. Marquis, J.-P. Desvergne, H. BouasLaurent, J. Org. Chem. 1995, 60, 7984-7996, and references cited therein; - [7m] E. C Constable, D. R. Smith, Tetrahedron 1996, 52, 935-940; - [7n] P. Belser, R. Dux, M. Baak, L. De Cola, V. Balzani, Angew. Chem. Int. Ed. Engl. 1995, 34, 595-598; - [7o] B. Henze, D. Marquis, P. Marsau, M. Cotrait, J.-P. Desvergne, Tetrahedron Lett. 1996, 31, 5499-5502.
    • (1996) Tetrahedron , vol.52 , pp. 935-940
    • Constable, E.C.1    Smith, D.R.2
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    • For references regarding the incorporation of anthracene derived subunits into supramolecular systems, see: [7a] A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218, and references cited therein; - [7b] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317; - [7c] G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Cryst. 1987, C43, 857-860; - [7d] L. Prodi, R. Ballardini, M. T. Gandolfi, V. Balzani, J.-P. Desvergne, H. Bouas-Laurent, J. Phys. Chem. 1991, 95, 2080-2083; - [7e] I. Willner, J. Rosengaus, Y. Eichen, New. J. Chem. 1991, 15, 55-64; - [7f] F. Effenberger, G. Gotz, P. Bauerle, Chem. Ber. 1992, 125, 941-950; - [7g] H. Hopf, R. Uttermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517; - [7h] A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature (London) 1993, 364, 42-44; - [7i] F. Fages, J.-P. Desvergne, K. Kampke, H. Bouas-Laurent, J.-M. Lehn, M. Meyer, A.-M. Albrecht-Gary, J. Am Chem. Soc. 1993, 115, 3658-3664; - [7j] L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza, T. Torres, J. Org. Chem. 1993, 58, 2009-2012; - [7k] M. Jorgensen, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larssen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993, 58, 2785-2790; - [7l] D. Marquis, J.-P. Desvergne, H. BouasLaurent, J. Org. Chem. 1995, 60, 7984-7996, and references cited therein; - [7m] E. C Constable, D. R. Smith, Tetrahedron 1996, 52, 935-940; - [7n] P. Belser, R. Dux, M. Baak, L. De Cola, V. Balzani, Angew. Chem. Int. Ed. Engl. 1995, 34, 595-598; - [7o] B. Henze, D. Marquis, P. Marsau, M. Cotrait, J.-P. Desvergne, Tetrahedron Lett. 1996, 31, 5499-5502.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 595-598
    • Belser, P.1    Dux, R.2    Baak, M.3    De Cola, L.4    Balzani, V.5
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    • 0030605872 scopus 로고    scopus 로고
    • For references regarding the incorporation of anthracene derived subunits into supramolecular systems, see: [7a] A. Castellan, M. Daney, J.-P. Desvergne, M.-H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218, and references cited therein; - [7b] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317; - [7c] G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Cryst. 1987, C43, 857-860; - [7d] L. Prodi, R. Ballardini, M. T. Gandolfi, V. Balzani, J.-P. Desvergne, H. Bouas-Laurent, J. Phys. Chem. 1991, 95, 2080-2083; - [7e] I. Willner, J. Rosengaus, Y. Eichen, New. J. Chem. 1991, 15, 55-64; - [7f] F. Effenberger, G. Gotz, P. Bauerle, Chem. Ber. 1992, 125, 941-950; - [7g] H. Hopf, R. Uttermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517; - [7h] A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature (London) 1993, 364, 42-44; - [7i] F. Fages, J.-P. Desvergne, K. Kampke, H. Bouas-Laurent, J.-M. Lehn, M. Meyer, A.-M. Albrecht-Gary, J. Am Chem. Soc. 1993, 115, 3658-3664; - [7j] L. Echegoyen, Y. Hafez, R. C. Lawson, J. de Mendoza, T. Torres, J. Org. Chem. 1993, 58, 2009-2012; - [7k] M. Jorgensen, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larssen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993, 58, 2785-2790; - [7l] D. Marquis, J.-P. Desvergne, H. BouasLaurent, J. Org. Chem. 1995, 60, 7984-7996, and references cited therein; - [7m] E. C Constable, D. R. Smith, Tetrahedron 1996, 52, 935-940; - [7n] P. Belser, R. Dux, M. Baak, L. De Cola, V. Balzani, Angew. Chem. Int. Ed. Engl. 1995, 34, 595-598; - [7o] B. Henze, D. Marquis, P. Marsau, M. Cotrait, J.-P. Desvergne, Tetrahedron Lett. 1996, 31, 5499-5502.
    • (1996) Tetrahedron Lett. , vol.31 , pp. 5499-5502
    • Henze, B.1    Marquis, D.2    Marsau, P.3    Cotrait, M.4    Desvergne, J.-P.5
  • 28
  • 43
    • 2842571529 scopus 로고    scopus 로고
    • note
    • c.
  • 47
    • 0001151973 scopus 로고
    • For previously reported examples of energy transfer from naphthalene to anthracene units in bichromophoric systems, see: J. Ferguson, A. W. -H. Mau, M. Puza, Molec. Phys. 1974, 28, 1457-1466.
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    • Ferguson, J.1    Mau, A.W.H.2    Puza, M.3
  • 51
    • 2842551501 scopus 로고    scopus 로고
    • note
    • -1), an observation which is consistent with the lack of constraints forcing the two interacting units to stay close together in an "along-side" geometry.


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