Amphiphilic cyclic fullerene bisadducts: Synthesis and Langmuir films at the air-water interface

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5747-5750

  Nierengarten, Jean François ^a   Schall, Corinne ^a   Nicoud, Jean François ^a   Heinrich, Benoît ^a   Guillon, Daniel ^a  

^a INSTITUT DE PHYSIQUE ET CHIMIE DES MATÉRIAUX DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMPHOPHILE; FULLERENE DERIVATIVE; WATER;

ARTICLE; CRYSTALLIZATION; CYCLIZATION; ENCAPSULATION; FILM; MOLECULAR INTERACTION; OPTICAL ROTATION; PHYSICAL CHEMISTRY; SYNTHESIS;

EID: 0032490971     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01134-4     Document Type: Article

References (20)

1. 1) Diederich, F.; Thilgen, C.; Science 1996, 271, 317-323; Prato, M.; J. Mater. Chem. 1997, 7, 1097-1109.
2. 1) Diederich, F.; Thilgen, C.; Science 1996, 271, 317-323; Prato, M.; J. Mater. Chem. 1997, 7, 1097-1109.
3. 2) a) Obeng, Y.S.; Bard, A.J.; J. Am. Chem. Soc. 1991, 113, 6279-6280; Mirkin, C.A.; Caldwell, W.B.; Tetrahedron 1996, 52, 5113-5130 and references cited therein;
4. 2) a) Obeng, Y.S.; Bard, A.J.; J. Am. Chem. Soc. 1991, 113, 6279-6280; Mirkin, C.A.; Caldwell, W.B.; Tetrahedron 1996, 52, 5113-5130 and references cited therein;
5. b) Chen, K.; Cadwell, W.B.; Mirkin, C.A. J. Am. Chem. Soc. 1993, 115, 1193-1194; Decher, G.; Nachr. Chem. Tech. Lab. 1993, 41, 793-800.
6. b) Chen, K.; Cadwell, W.B.; Mirkin, C.A. J. Am. Chem. Soc. 1993, 115, 1193-1194; Decher, G.; Nachr. Chem. Tech. Lab. 1993, 41, 793-800.
7. 3) Jonas, U.; Cardullo, F.; Belik, P.; Diederich, F.; Gügel, A.; Harth, E.; Herrmann, A.; Isaacs, L.; Müllen, K.; Ringsdorf, H.; Thilgen, C.; Uhlmann, P.; Vasella, A.; Waldraff, C.A.A.; Walter, M.; Chem. Eur. J. 1995, 1, 243-251 and references cited therein; Patel, H.M.; Didymus, J.M.; Wong, K.K.W.; Hirsch, A.; Skiebe, A.; Lamparth, I.; Mann, S.; J. Chem. Soc., Chem. Commun. 1996, 611-612; Wang, S.; Leblanc, R.M.; Arias, F.; Echegoyen, L.; Langmuir 1997, 13, 1672-1676; Wang, P.; Chen, B.; Metzger, R.M.; Da Ros, T.; Prato, M.; J. Mat. Chem. 1997, 7, 2397-2400; Zhou, D.; Ashwell, G.J.; Rajan, R.; Gan, L.; Luo, C.; Huang, C.; J. Chem. Soc., Faraday Trans. 1997, 93, 2077-2081.
8. 3) Jonas, U.; Cardullo, F.; Belik, P.; Diederich, F.; Gügel, A.; Harth, E.; Herrmann, A.; Isaacs, L.; Müllen, K.; Ringsdorf, H.; Thilgen, C.; Uhlmann, P.; Vasella, A.; Waldraff, C.A.A.; Walter, M.; Chem. Eur. J. 1995, 1, 243-251 and references cited therein; Patel, H.M.; Didymus, J.M.; Wong, K.K.W.; Hirsch, A.; Skiebe, A.; Lamparth, I.; Mann, S.; J. Chem. Soc., Chem. Commun. 1996, 611-612; Wang, S.; Leblanc, R.M.; Arias, F.; Echegoyen, L.; Langmuir 1997, 13, 1672-1676; Wang, P.; Chen, B.; Metzger, R.M.; Da Ros, T.; Prato, M.; J. Mat. Chem. 1997, 7, 2397-2400; Zhou, D.; Ashwell, G.J.; Rajan, R.; Gan, L.; Luo, C.; Huang, C.; J. Chem. Soc., Faraday Trans. 1997, 93, 2077-2081.
9. 3) Jonas, U.; Cardullo, F.; Belik, P.; Diederich, F.; Gügel, A.; Harth, E.; Herrmann, A.; Isaacs, L.; Müllen, K.; Ringsdorf, H.; Thilgen, C.; Uhlmann, P.; Vasella, A.; Waldraff, C.A.A.; Walter, M.; Chem. Eur. J. 1995, 1, 243-251 and references cited therein; Patel, H.M.; Didymus, J.M.; Wong, K.K.W.; Hirsch, A.; Skiebe, A.; Lamparth, I.; Mann, S.; J. Chem. Soc., Chem. Commun. 1996, 611-612; Wang, S.; Leblanc, R.M.; Arias, F.; Echegoyen, L.; Langmuir 1997, 13, 1672-1676; Wang, P.; Chen, B.; Metzger, R.M.; Da Ros, T.; Prato, M.; J. Mat. Chem. 1997, 7, 2397-2400; Zhou, D.; Ashwell, G.J.; Rajan, R.; Gan, L.; Luo, C.; Huang, C.; J. Chem. Soc., Faraday Trans. 1997, 93, 2077-2081.
10. 3) Jonas, U.; Cardullo, F.; Belik, P.; Diederich, F.; Gügel, A.; Harth, E.; Herrmann, A.; Isaacs, L.; Müllen, K.; Ringsdorf, H.; Thilgen, C.; Uhlmann, P.; Vasella, A.; Waldraff, C.A.A.; Walter, M.; Chem. Eur. J. 1995, 1, 243-251 and references cited therein; Patel, H.M.; Didymus, J.M.; Wong, K.K.W.; Hirsch, A.; Skiebe, A.; Lamparth, I.; Mann, S.; J. Chem. Soc., Chem. Commun. 1996, 611-612; Wang, S.; Leblanc, R.M.; Arias, F.; Echegoyen, L.; Langmuir 1997, 13, 1672-1676; Wang, P.; Chen, B.; Metzger, R.M.; Da Ros, T.; Prato, M.; J. Mat. Chem. 1997, 7, 2397-2400; Zhou, D.; Ashwell, G.J.; Rajan, R.; Gan, L.; Luo, C.; Huang, C.; J. Chem. Soc., Faraday Trans. 1997, 93, 2077-2081.
11. 3) Jonas, U.; Cardullo, F.; Belik, P.; Diederich, F.; Gügel, A.; Harth, E.; Herrmann, A.; Isaacs, L.; Müllen, K.; Ringsdorf, H.; Thilgen, C.; Uhlmann, P.; Vasella, A.; Waldraff, C.A.A.; Walter, M.; Chem. Eur. J. 1995, 1, 243-251 and references cited therein; Patel, H.M.; Didymus, J.M.; Wong, K.K.W.; Hirsch, A.; Skiebe, A.; Lamparth, I.; Mann, S.; J. Chem. Soc., Chem. Commun. 1996, 611-612; Wang, S.; Leblanc, R.M.; Arias, F.; Echegoyen, L.; Langmuir 1997, 13, 1672-1676; Wang, P.; Chen, B.; Metzger, R.M.; Da Ros, T.; Prato, M.; J. Mat. Chem. 1997, 7, 2397-2400; Zhou, D.; Ashwell, G.J.; Rajan, R.; Gan, L.; Luo, C.; Huang, C.; J. Chem. Soc., Faraday Trans. 1997, 93, 2077-2081.
12. 4) During the preparation of this manuscript, the synthesis of amphiphilic fullerene-dendrimer conjugates with a reversible compression/expansion behavior has been reported, see: Cardullo, F.; Diederich, F.; Echegoyen, L.; Habicher, T.; Jayaraman, N.; Leblanc, R.M.; Stoddart, J.F.; Wang, S.; Langmuir 1998, 14, 1955-1959.
13. 5) Nierengarten, J.-F.; Schall, C.; Nicoud, J.-F.; Angew. Chem., in press.
14. 6) Nierengarten, J.-F.; Nicoud, J.-F.; Tetrahedron Lett. 1997, 38, 7737-7740.
15. 7) a) Nierengarten, J.-F.; Gramlich, V.; Cardullo, F.; Diederich, F.; Angew. Chem. Int. Ed. Engl. 1996, 35, 2101-2103;
16. b) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M.; Helv. Chim. Acta, 1997, 80, 2238-2276.
17. 8) For a detailed discussion on the regio-and diastereoselectivity of the macrocyclisation reaction on the fullerene core, see ref. 7b.
18. 14: C 82.22, H 6.17; found: C 82.15, H 6.37.
19. 10) Hirsch, A.; Lamparth, I.S.; Karfunkel, H.R.; Angew. Chem. Int. Ed. Engl. 1994, 33, 437-438.
20. 11) Ibn-Elhaj, M.; Möhwald, H.; Cherkaoui, M.Z.; Zniber, R.; Langmuir 1998, 14, 504-516.