Synthesis and electronic properties of tetrakis[4-(pyrimidyl)phenyl]methanes - A novel class of electronically active nanometer-sized scaffolds

European Journal of Organic Chemistry

Volumn , Issue 19, 2000, Pages 3305-3312

  Zimmermann, Thomas J ^a   Freundel, Oliver ^a   Gompper, Rudolf ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cyclic voltammetry; Cyclizations; Heterocycles; Nanostructures; Redox chemistry

Indexed keywords

PYRIMIDINE DERIVATIVE; TETRAKIS[4 (PYRIMIDYL)PHENYL METHANE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIC POTENTIOMETRY; CYCLIZATION; ELECTRONICS; FLAME PHOTOMETRY; OXIDATION REDUCTION REACTION; POLYMERIZATION; POTENTIOMETRY; SPECTROSCOPY; SYNTHESIS;

EID: 0033770729     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200010)2000:19<3305::AID-EJOC3305>3.0.CO;2-C     Document Type: Article

References (39)

1. [1a] D. A. Tomalia, A. M. Naylor, W. A. Goddard, Angew. Chem. 1990, 102, 119-157; Angew. Chem. Int. Ed Engl. 1990, 29, 113-151.
2. D. A. Tomalia, A. M. Naylor, W. A. Goddard, Angew. Chem. 1990, 102, 119-157; Angew. Chem. Int. Ed Engl. 1990, 29, 113-151.
3. [1b] C. J. Hawker, J. M. J. Frechet, J. Am. Chem. Soc. 1990, 112, 7638-7647.
4. [1c] A. J. Berresheim, M. Müller, K. Müllen, Chem. Rev. 1999, 99, 1747-1786.
5. [1d] P. F. H. Schwab, M. D. Levin, J. Michl, Chem. Rev. 1999, 99, 1863-1934.
6. For a very recent review on dendrimers, see e.g.: M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955; Angew. Chem. Int. Ed. Engl. 1999, 38, 885-905.
7. For a very recent review on dendrimers, see e.g.: M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955; Angew. Chem. Int. Ed. Engl. 1999, 38, 885-905.
8. [3a] D. S. Reddy, D. C. Craig, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4090-4093, and references cited therein.
9. [3b] J. H. Wendorff, Nachr. Chem. Techn. Lab. 1995, 43, 310.
10. For recent and significant contributions to the synthesis of tetraarylmethanes, see e.g.: [4a] L. M. Wilson, A. C. Griffin, J. Mater. Chem. 1993, 3, 991-994.
11. [4b] S. Sengupta, S. K. Sadhukhan, Tetrahedron Lett. 1998, 39, 1237-1238.
12. [4c] S. Sengupta, Saumitra, S. K. Sadhukhan, Tetrahedron Lett. 1999, 40, 9157-9161.
13. [4d] O. Mongin, A. Gossauer, Tetrahedron 1997, 53, 6835-6846.
14. S. Eldin, J. F. Liebman, L. D. Reynolds, P. Dowd, Tetrahedron Lett. 1992, 33, 4525-4528.
15. [6a] S. Brandl, R. Gompper, K. Polborn, J. Prakt. Chem. 1996, 338, 451-459.
16. [6b] R. Gompper, H.-J. Mair, K. Polborn, Synthesis 1997, 696-718.
17. Quantum CAChe 3.0 Program, Oxford Molecular Group, 1997.
18. J. J. Aaron, M. Maafi, C. Parkanyi, C. Boniface, Spectrochim. Acta, Part A 1995, 51, 603-616.
19. P. W. Atkins, Quanten, VCH, Weinheim, 1993, pp. 93.
20. [10a] S. Marguet, D. Markovitsi, P. Millie, H. Sigal, S. Kumar, J. Phys. Chem. 1998, B102, 4697-4710.
21. [10b] D. Markovitsi, A. Germain, P. Millie, P. Lecuyer, L. K. Gallos, P. Argyrakis, H. Bengs, H. Ringsdorf, J. Phys. Chem. 1995, 99, 1005-1017.
22. J. Heinze, Angew. Chem. 1984, 96, 823-840; Angew. Chem. Int. Ed. Engl. 1984, 23, 831-848.
23. J. Heinze, Angew. Chem. 1984, 96, 823-840; Angew. Chem. Int. Ed. Engl. 1984, 23, 831-848.
24. [12a] J. D. Young, N. L. Bauld, Tetrahedron Lett. 1971, 25, 2251-2254. For preparative studies on this effect, see e.g.:
25. [12b] E. Grovenstein, A. M. Bhatti, F. A. Plagge, Y. M. Heinrich, T. H. Longfield, J. Singh, D. VanDerveer, Organometallics 1990, 9, 2587-2593.
26. [13a] A. Ronlan, O. Hammerich, V. D. Parker, J. Am. Chem. Soc. 1973, 95, 7132-7138.
27. [13b] A. Ronlan, V. D. Parker, J. Org. Chem. 1974, 39, 1014-1016.
28. B. Knight, N. Martin, T. Ohno, E. Orti, C. Rovira, J. Veciana, J. Vidal-Gancedo, P. Viruela, R. Viruela, F. Wudl, J. Am. Chem. Soc. 1997, 119, 9871-9882.
29. E. V. Brown, Synthesis 1975, 358-375.
30. D. R. Lloyd, K. S. Tucker, D. R. Marshall, J. Chem. Soc., Perkin Trans. 1 1981, 726-735.
31. Various editors, Organikum, 14th ed., VEB Deutscher Verlag der Wissenschaften, Berlin, 1993.
32. B. F. Hoskins, R. Robson, J. Am. Chem. Soc. 1990, 112, 1546-1554.
33. [19a] Z. Arnold, Collect. Czech. Chem. Commun. 1963, 28, 863-866.
34. [19b] H. Niedrich, H.-U. Heyne, E. Schrötter, H.-J. Jänsch, H. J. Heidrich, G. Faust, D. Lohmann, Pharmazie 1986, 41, 173-175.
35. [19c] Z. Arnold, Collect. Czech. Chem. Commun. 1965, 38, 2783-2792.
36. S. N. Balasubrahmanyam. A. S. Radhakrishna, J. Chem. Soc., Perkin Trans. 2 1977, 1388-1390.
37. D. Lloyd, C. Reichardt, M. Struthers, Liebigs Ann. Chem. 1986, 1368-1379.
38. [22a] S. Kirstein, H. Möhwald, Adv. Mater. 1995, 7, 460-463.
39. [22b] O. Wörz, G. Scheibe, Z. Naturforsch., Teil B 1969, 24, 381-390.