Polycyclic Aromatic Hydrocarbons in the Nanometer Range

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 18, 1997, Pages 1996-1998

  Schlicke, Benedikt ^a   Schlüter, A Dieter ^a   Hauser, Petra ^b   Heinze, Jürgen ^b  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b NONE

Author keywords

Arenes; Cyclic voltammetry; Diels Alder reactions; Fluorescence; Polycycles

Indexed keywords

EID: 0030869491     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199719961     Document Type: Article

References (24)

1. See, for example, A. Hirsch, The Chemistry of Fullerenes, Thieme, Stuttgart, 1994.
2. See, for example, Conjugated Polymers (Eds.: J.-L. Brédaa, R. Silbey), Kluwer, Dordrecht, 1991.
3. a) A.-D. Schlüter, Adv. Mater. 1991, 3, 282;
4. b) M. Löffler, A.-D. Schlüter, K. Gessler, W. Saenger, J.-M. Toussaint, J.-L. Brédas, Angew. Chem. 1994, 106, 2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2209;
5. b) M. Löffler, A.-D. Schlüter, K. Gessler, W. Saenger, J.-M. Toussaint, J.-L. Brédas, Angew. Chem. 1994, 106, 2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2209;
6. c) B. Schlicke, H. Schirmer, A.-D. Schlüter, Adv. Mater. 1995, 7, 544;
7. d) B. Schlicke, J. Frahn, A.-D. Schlüter, Synth. Met. 1996, 83, 173-176.
8. For an alternative approach to double-stranded, unsaturated polymers, see U. Scherf, K. Müllen, Synthesis 1992, 23.
9. Compound 4 was prepared according to the method of C. F. Allen, Chem. Rev. 1962, 62, 653. See also B. Schlicke, A.-D. Schlüter, Synlett 1996, 425.
10. Compound 4 was prepared according to the method of C. F. Allen, Chem. Rev. 1962, 62, 653. See also B. Schlicke, A.-D. Schlüter, Synlett 1996, 425.
11. H. Hart, D. Ok, J. Org. Chem. 1986, 51, 979. See also M. Löffler, A.-D. Schlüter, Synlett 1994, 75.
12. H. Hart, D. Ok, J. Org. Chem. 1986, 51, 979. See also M. Löffler, A.-D. Schlüter, Synlett 1994, 75.
13. The LDI-TOF spectra of 6,7, and other related compounds show, besides the molecular ion peak (low intensity), patterns of signals with a Gaussian type distribution at somewhat lower masses (relatively high intensity). The peaks of these patterns are separated by a constant m/e = 28 Da. The reason for this finding is not yet understood. A possible systematic distribution of molecular finding caused by an inadvertent employment of reagents with an even distribution of methylene groups in the alkyl chains is unlikely. The alkyl chains are introduced into the whole sequence as bromides and alcohols (see Refs. [3d, 5]), the purity of which was greater than 98% (checked by (GC)).
14. Despite several attempts we were not able to get correct analytical data from compound 6; the values for H were always slightly too small.
15. J. Heinze, Angew. Chem. 1984, 96, 823; Angew. Chem. Int. Ed. Engl. 1984, 23, 831.
16. J. Heinze, Angew. Chem. 1984, 96, 823; Angew. Chem. Int. Ed. Engl. 1984, 23, 831.
17. Q. Xie, E. Pérez-Cordero, L. Echegoyen, J. Am. Chem. Soc. 1992, 114, 3978; Y. Ohsawa, T. Saji, J. Chem. Soc. Chem. Commun. 1992, 781; K. Meerholz, P. Tschunky, J. Heinze, J. Electroanal. 1993, 347, 425.
18. Q. Xie, E. Pérez-Cordero, L. Echegoyen, J. Am. Chem. Soc. 1992, 114, 3978; Y. Ohsawa, T. Saji, J. Chem. Soc. Chem. Commun. 1992, 781; K. Meerholz, P. Tschunky, J. Heinze, J. Electroanal. 1993, 347, 425.
19. Q. Xie, E. Pérez-Cordero, L. Echegoyen, J. Am. Chem. Soc. 1992, 114, 3978; Y. Ohsawa, T. Saji, J. Chem. Soc. Chem. Commun. 1992, 781; K. Meerholz, P. Tschunky, J. Heinze, J. Electroanal. 1993, 347, 425.
20. For comparison, see A. Bohnen, K.-H. Koch, W. Lüttke, K. Müllen, Angew. Chem. 1990, 102, 548; Angew. Chem. Int. Ed. Engl. 1990, 29, 525.
21. For comparison, see A. Bohnen, K.-H. Koch, W. Lüttke, K. Müllen, Angew. Chem. 1990, 102, 548; Angew. Chem. Int. Ed. Engl. 1990, 29, 525.
22. The reason for the weak fluorescence of 7 is presently under investigation.
23. See, for example, W. Schmidt, Optische Spektroskopie, VCH, Weinheim, 1994
24. The lengths were calculated with the program Spartan Silicon Graphics, Version 4.1.1., on the assumption that conformations are planar. Hydrogen atoms were disregarded.