Abstract
The state of the art in heterofullerene chemistry and physics is reviewed with emphasis on azafullerenes. The macroscopic synthetic methods that have been developed for aza[60] fullerene compounds since 1995 have led to a whole new and rich area in the science of fullerenes: cage modification chemistry. The synthetic routes towards aza[60]fullerene and its derivatives are reviewed in Sect. 2. The synthetic routes for aza[70]fullerene and its derivatives are summarized in Sect. 3. Section 4 comprises the theoretical and experimental work on the physicochemical properties of azafullerene compounds. Finally, in Sect. 5, the literature regarding heterofullerenes other than monoazafullerenes is reviewed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE (1985) Nature 318:162
Krätchmer WA, Lamb LD, Fostiropoulos K, Huffman DR (1990) Nature 347:354
Guo T, Jin C, Smalley RE (1991) J Phys Chem 95:4948
Hummelen JC, Wudl F (1995) Unpublished results
Lamparth I, Nuber B, Schick G, Skiebe A Grösser T, Hirsch A (1995) Angew Chem Int Ed Engl 34:2257
Averdung J, Luftmann H, Schlachter I, Mattay J (1995) Tetrahedron 51:6977
Hummelen JC, Knight B, Pavlovich J, González R, Wudl F (1995) Science 269:1554
Nuber B, Hirsch A (1996) J Chem Soc Chem Commun 1421
Tenne R (1995) Adv Mater 7:965
Huckzo A (1997) Fullerene Sci Technol 5:1091
Huckzo A (1997) Wiad Chem 51:27 (Chem Abstr 127:50671)
Ying ZC, Zhu JG, Compton RN, Allard Jr LF, Hettich RL, Haufler RE (1997) ACS Symp Ser 679:169 (Chem Abstr 127:365278)
Cao B, Zhou X, Gu Z (1997) Huaxue Tongbao 1 (Chem Abstr 128:109852)
Prassides K (1997) Curr Opin Solid State Mater Sci 2:433
Kuzmany H (1998) Phys Unserer Zeit 29:16
Hirsch A (1997) J Phys Chem Solids 58:1729
Mattay J, Torres-Garcia G, Averdung J, Wolff C, Schlachter I, Luftmann H, Siedschlag C, Luger P, Ramm M (1997) J Phys Chem Solids 58:1929
Averdung J, Torres-Garcia G, Luftmann H, Schlachter I, Mattay J (1996) Fullerene Sci Technol 4:633
Wudl F, Bellavia-Lund C, Collins T, González M, Hicks RG, Hummelen JC, Keshavarz-K M, Sastre A, Srdanov G (1996) Proc Robert A Welch Found Conf Chem Res 40th 131–138:87
Bellavia-Lund C, Hummelen JC, Keshavarz-K M, González R, Wudl F (1997) J Phys Chem Solids 58:1983
Bellavia-Lund C, Keshavarz-K M, González R, Hummelen JC, Hicks R, Wudl F (1997) Phosphorus, Sulfur, and Silicon 120+121:107
Godly EW, Taylor R (1997) Pure Appl Chem 69:1411
Pradeep T, Vijayakrishnan V, Santra AK, Rao CNR (1991) J Phys Chem 95:10564
Rao CNR, Pradeep T, Seshadri R, Govindaraj A (1992) Ind J Chem 31 A + B:F27
Christian JF, Wan Z, Anderson SL (1992) J Phys Chem 96:10597
Glenis S, Cooke S, Chen X, Labes MM (1994) Chem Mater 6:1850
Glenis S, Cooke S, Chen X, Labes MM (1995) Synth Metals 70:1313
Yu R, Zhan M, Cheng D, Yang S, Liu Z, Zheng L (1995) J Phys Chem 99:1818
Zhang MX, Yu RQ, Wang YH, Yang SY, Cheng DD, Liu CY, Zheng LS (1995) Gaodeng Xuexiao Huaxue Xuebao 16:1780 (Chem Abstr 124:217583)
Xie E, Gong J, Xu C, Chen G (1996) Bandaoti Xuebao 17:177 (Chem Abstr 125:209454)
Piechota J, Byszewski P, Jablonski R, Antonova K (1996) Fullerene Sci Technol 4:491
Ying ZC, Hettich RL, Compton RN, Haufler RE (1996) J Phys B:At Mol Opt Phys 29:4935
Ying ZC, Zhu JG, Compton RN, Allard LF Jr, Hettich RL, Haufler RE (1997) ACS Symp Ser 679:169 (Chem Abstr 127:365278)
Yoshida T, Eguchi K, Yoshie K (1992) Eur Pat Appl (Chem Abstr 118:194586)
Prato M, Chan LQ, Wudl F, Lucchini V (1993) J Am Chem Soc 115:1148
Nuber B, Hampel F, Hirsch A (1995) J Chem Soc Chem Commun 1799
Grösser T, Prato M, Lucchini V, Hirsch A, Wudl F (1995) Angew Chem Int Ed Engl 34:1343
Prato M, Wudl F, Grösser T, Hirsch A (1995) German Patent DE 95-19507502 (to Hoechst A.-G.)
Shiu LL, Chien KM, Liu TY, Lin TI Her GR, Luh TY (1995) J Chem Soc Chem Commun 1159
Schick G, Hirsch A, Mauser H, Clark T (1996) Chem Eur J 2:935
Shen C, Yu H, Juo CG, Chien KM, Her GR, Luh TY (1997) Chem Eur J 3:744
Shen CKF, Chien KM, Juo CG, Her GR, Luh TY (1996) J Org Chem 61:9242
Shen CKF, Chien KM, Juo CG, Her GR, Luh TY (1997) J Org Chem 62:4548
Banks MR, Cadogan JIG, Gosney I, Hodgson PKG, Langridge-Smith PRR, Millar JRA, Parkinson JA, Rankin DWH, Taylor AT (1995) J Chem Soc Chem Commun 887
Schick G, Grösser T, Hirsch A (1995) J Chem Soc Chem Commun 2289
Averdung J, Mattay J, Jacobi D, Abraham W (1995) Tetrahedron 51:2543
Averdung J, Luftmann H, Mattay J, Claus K.-U, Abraham W (1995) Tetrahedron Lett 36:2957
Mattay J, Averdung J, Luftmann H, Schlachter I (1995) German Patent DE 95-19506230 (Chem Abstr 125:221612; 125:247605)
Banks MR, Gosney I, Hodgson PKG, Langridge-Smith PRR, Millar JRA, Taylor AT (1995) J Chem Soc Chem Commun 885
Averdung J, Wolff C, Mattay J (1996) Tetrahedron Lett 37:4683
Averdung J, Mattay J (1996) Tetrahedron 52:5407
Ihisda T, Tanaka K, Nogami T (1994) Chem Lett 561
Yan M, Cai SX, Keana JF (1994) J Org Chem 59:5951
Banks MR, Cadogan JIG, Gosney I, Hodgson PKG, Langridge-Smith PRR, Rankin DWH (1994) J Chem Soc Chem Commun 1365
Kuwashima S, Kubota M, Kushida K, Ishida T, Ohashi M, Nogami T (1994) Tetrahedron Lett 35:4371
Hirsch A (1994) The chemistry of the fullerenes. Thieme, Stuttgart
Hirsch A, Lamparth I, Grösser T, Prato M, Lucchini V, Wudl F (1996) NATO ASI Ser, Ser E 316 [Chemical Physics of Fullerenes 10 (and 5) Years Later, p 267]
Mattay J, Siedschlag C, Torres-Garcia G, Ulmer L, Wolff C, Fujitsuka M, Watanabe A, Ito O, Luftmann H (1997) Proc Electrochem Soc 97 14:326
Averdung J, Albrecht E, Luftmann H, Schlachter I, Mattay J, Claus K.-U, Jakobi D, Abraham W (1995) Proc Electrochem Soc 95 10:1164
Averdung J, Mattay J (1997) Prax Naturwiss Chem 46:28
Averdung J, Gerkensmeier T, Ito O, Luftmann H, Luger P, Schlachter I, Siedschlag C, Torres-Garcia G, Mattay J (1997) In: Kuzmany H (ed) Fullerenes Fullerene Nanostruct, Proc Int Wintersch Electron Prop Novel Mater 10th, World Scientific Singapore, p 509
Hummelen JC, Prato M, Wudl F (1995) J Am Chem Soc 117:7003
O’Brien S, Heath JR, Curl RF, Smalley RE (1988) J Chem Phys 88:220
Hummelen JC, Keshavarz-K M, van Dongen JLJ, Janssen RAJ, Meijer EW, Wudl F (1998) J Chem Soc Chem Commun 281
Bellavia-Lund C, Keshavarz-K M, Collins T, Wudl F (1997) J Am Chem Soc 119:8101
Sastre A, Keshavarz-K M, Wudl F Unpublished results
Keshavarz-K M, González R, Hicks RG, Srdanov G, Srdanov VI, Collins TA, Hummelen JC, Bellavia-Lund C, Pavlovich J, Wudl F (1996) Nature 383:147
Nuber B, Hirsch A (1998) J Chem Soc Chem Commun 405
Bellavia-Lund C, González R, Hummelen JC, Hicks RG, Sastre A, Wudl F (1997) J Am Chem Soc 119:2946
Reuther U, Hirsch A (1998) J Chem Soc Chem Comm 1401
Birkett PR, Avent AG, Darwish AD, Kroto HW, Taylor R, Walton DRM (1993) J Chem Soc Chem Commun 1230
Bellavia-Lund C, Wudl F (1997) J Am Chem Soc 119:943
Smith III A, Strongin R, Brard L, Furst G, Romanow W, Owens K, Goldschmidt R (1995) J Am Chem Soc 117:5492 and references within
Hassner AJ (1968) J Org Chem 33:2684
Hawkins JM, Meyer A, Solow M (1993) J Am Chem Soc 115:7499
Bellavia-Lund (1997) Thesis UCSB, Santa Barbara CA (USA)
Hasharoni K, Bellavia-Lund C, Keshavarz-K M, Srdanov G, Wudl F (1997) J Am Chem Soc 119:11128
De la Cruz P, Wudl F, Bellavia-Lund C (1998) Presented at the 193rd Meeting of the ECS, San Diego, CA
Wang S-H, Chen F, Fann Y-C, Kashani M, Malaty M, Jansen SA (1995) J Phys Chem 99:6801
Andreoni W, Gygi F, Parrinello M (1992) Chem Phys Lett 190:159
Andreoni W, Gygi F, Parrinello M (1992) NATO ASI Ser, Ser C 374:333
Kurita N, Kobayashi K, Kumahora H, Tago K, Ozawa K (1992) Chem Phys Lett 198:95
Liu J, Gu B, Han R (1992) Solid Sate Commun 84:807
Rosen A, Oestling D (1992) Mater Res Soc Symp Proc 270:141
Chen F, Singh D, Jansen SA (1993) J Phys Chem 97:10958
Breslavskaya NN, D’yachkov PN (1994) Koord Khim 20:803 (Chem Abstr 123:112384)
Dong J, Jiang J, Wang ZD, Xing DY (1995) Phys Rev B 51:1977
Dong J, Jiang J,Yu J, Wang ZD, Xing DY (1995) Phys Rev B 52:9066
Jiang J, Dong J, Xing DY (1997) Solid State Commun 101:537
Xu Q, Jiang J, Dong J, Xing DY (1996) Phys Status Solidi B 193:205
Jiang J, Dong J, Xu Q, Xing DY (1996) Z Phys D:At Mol Clusters 37:341
Rustagi KC, Ramaniah LM, Nair SV (1992) Int J Mod Phys B 6:3941
Vancik H, Babic D, Trinajstic N (1995) Fullerene Sci Technol 3:305
Piechota J, Byszewski P (1997) Z Phys Chem 200:147
Andreoni W, Curioni A (1996) In: Kuzmany H (ed) Fullerenes Fullerene Nanotruct, Proc Int Wintersch Electron Prop Novel Mater, 10th World Scientific Singapore, p 359
Bühl M, Curioni A, Andreoni W (1997) Chem Phys Lett 274:231
Curioni A, Andreoni W (1998) In: Kuzmany H, Fink J, Mehring M, Roth S (eds) Molecular Nanostructures, World Scientific Singapore, p 81
Andreoni W, Curioni A, Holczer K, Prassides K, Keshavarz-K M, Hummelen JC, Wudl F (1996) J Am Chem Soc 118:11335
Gruss A, Dinse K-P, Hirsch A, Nuber B, Reuther U (1997) J Am Chem Soc 119:8728
Hasharoni K, Bellavia-Lund C, Keshavarz-K M, Srdanov G, Wudl F (1997) J Am Chem Soc 119:11128
Allemand P-M, Srdanov G, Koch A, Khemani K, Wudl F, Rubin Y, Diederich M, Alvarez MM, Anz SJ, Whetten RL (1991) J Am Chem Soc 113:2780
Janssen RAJ, Hummelen JC, Lee K, Pakbaz K, Sariciftci NS, Heeger AJ, Wudl F (1995) J Chem Phys 103:788
Brown CM, Cristofilini L, Kordatos K, Prassides K, Bellavia C, González R, Keshavarz K, Wudl F, Cheetham AK, Zhang JP, Andreoni W, Curioni A, Fitch AN, Pattison P (1996) Chem Mater 8:2548
Prassides K, Keshavarz-K M, Beer E, Bellavia C, González R, Murata Y, Wudl F, Cheetham AK, Zhang JP (1996) Chem Mater 8:2405
Prassides K, Wudl F, Andreoni W (1997) Fullerene Sci Technol 5:801
Brown CM, Beer E, Bellavia C, Cristofolini L, González R, Hanfland M, Häusermann D, Keshavarz-K M, Kordatos K, Prassides K, Wudl F (1996) J Am Chem Soc 118:8715
Prassides K, Keshavarz-KM, Hummelen JC, Andreoni W, Giannozzi P, Beer E, Bellavia C, Cristofilini L, González R, Lappas A, Murata Y, Malecki M, Srdanov V, Wudl F (1996) Science 271:1833
Fleming RM, Ramirez AP, Rosseinsky MJ, Murphy DW, Haddon RC, Zahurak SM, Makhija AV (1991) Nature 352:787
Tanigaki K, Ebbesen TW, Saito S, Mizuki J, Tsai JS, Kubu Y, Kuroshima S (1991) Nature 352:222
Srdanov, V (1996) unpublished results, Santa Barbara
Schwarz H (1996) unpublished results, Berlin
Thompson JD (1996) unpublished results, Los Alamos National Laboratory
Prassides K, Kordatos K (1996–1998) unpublished results, Sussex
Kordatos K, Brown CM, Prassides K, Bellavia-Lund C, de la Cpruz P, Wudl F, Thompson JD, Fitch AN (1998) In: Kuzmany H, Fink J, Mehring M, Roth S (eds) Molecular Nanostructures World Scientific Singapore, p 73
Pichler T, Knupfer M, Golden M, Haffner S, Friedlein R, Fink J, Andreoni W, Curioni A, Keshavarz-K M, Bellavia-Lund C, Sastre A, Hummelen JC, Wudl F (1997) Phys Rev Lett 78:4249
Pichler T, Knupfer M, Golden M, Fink J, Winter J, Haluska M, Kuzmany H, Keshavarz -K M, Bellavia-Lund C (1997) Appl Phys A: Mater Sci Process A64:301
Pichler T, Knupfer M, Friedlein R, Haffner S, Umlauf B, Golden M, Knauff O, Bauer H-D, Fink J, Keshavarz-K M, Bellavia-Lund C, Sastre A, Hummelen JC, Wudl F (1997) Synth Met 86:2313
Haffner S, Pichler T, Knupfer M, Umlauf B, Friedlein R, Golden MS, Fink J, Keshavarz -K M, Bellavia-Lund C, Sastre A, Hummelen JC, Wudl F (1998) Eur Phys J B 1:11
Golden MS, Pichler T, Knupfer M, Friedlein R, Haffner S, Fink J, Andreoni W, Curioni A, Keshavarz -K M, Bellavia-Lund C, Sastre A, Hummelen JC, Wudl F (1998) In: Kuzmany H, Fink J, Mehring M, Roth S (eds) Molecular Nanostructures World Scientific Singapore, p86
Malachesky PA (1969) Anal Chem 41:1493
Xie FA, Echegoyen L (1993) J Am Chem Soc 115:9818
Itaya K, Bard AJ, Szwarc M (1978) Z Phys Chem (Munich) 112:1
Guo T, Jin C, Smalley RE (1991) J Phys Chem 95:4948
Chai Y, Guo T, Jin C, Haufler RE, Chibante LPF, Fure J, Wang L, Alford JM, Smalley RE (1991) J Phys Chem 95:7564
Smalley RE (1991) In: Hammond GS, Kuck VJ (eds) Large carbon clusters. ACS, Washington, DC, p 199
Smalley RE (1992) In: Hammond GS, Kuck VJ (eds) Fullerenes: synthesis, properties, and chemistry of large carbon clusters. ACS Symposium Series 481, p 141
Muhr H-J, Nesper R, Schnyder B, Kötz R (1996) Chem Phys Lett 249:399
Cau B, Zhou X, Shi Z, Jin Z, Gu Z, Xiao H, Wang J (1997) Wuli Huaxue Xuebao 13:204 (ChemAbstr 126:317406)
Kurita N, Kobayashi K, Kumahora H, Tago K, Ozawa K (1992) Chem Phys Lett 198:95
Kurita N, Kobayashi K, Kumahora H, Tago K (1993) Phys Rev B 48:4850
Kurita N, Kobayashi K, Kumahora H, Tago K (1993) Fullerene Sci Technol 1:319
Liu M, Wang ZD, Dong J, Xing DY (1995) Z Phys B 97:433
Xu Q, Dong J, Jiang J, Xing DY (1996) J Phys B: At Mol Opt Phys 29:1563
Xu Q, Dong JM, Jiang J, Xing DY (1996) Acta Phys Sin (overseas edn) 5:175 (Chem Abstr 126:80155)
Chen Q, Lin J (1997) Jiegou Huaxue 16:445 (Chem Abstr 128:93396)
Xia X, Jelski DA, Bowser JR, George TF (1992) J Am Chem Soc 114:6493
Miyamoto Y, Hamada N, Oshiyama A, Saito S (1992) Phys Rev B 46:1749
Zou Y, Wang Z, Li W (1997) J Phys Chem Solids 58:1657
Karfunkel HR, Dressler T, Hirsch A (1992) J Comp-Aided Mol Design 6:521
Bühl M (1995) Chem Phys Lett 242:580
Esfarjani K, Ohno K, Kawazoe Y (1994) Phys Rev B 50:17830
Esfarjani K, Ohno K, Kawazoe Y (1996) Solid State Commun 97:539
Esfarjani K, Ohno K, Kawazoe Y (1996) Surf Rev Lett 3:747
Clemmer DE, Hunter JM, Shelimov KB, Jarrold MF (1994) Nature 372:248
Glenis S, Cooke S, Chen X, Labes MM (1996) Chem Mater 8:123
Christian JF, Wan Z, Anderson SL (1992) Chem Phys Lett 199:373
Jelski DA, Bowser JR, James R, Xia X, Xinfu G, Gao J, George TF (1993) J Cluster Sci 4:173
Kimura T, Sugai T, Shinohara H (1996) Chem Phys Lett 256:269
Oeste FD (1991) German Patents DE 91-4114536 910503 (ChemAbstr 117:91076) and DE 91-4128357 910827 (ChemAbstr 120:22451)
Jansen M, Peters G (1991) German Patent DE 91-413959 7911130 (ChemAbstr 119:75799)
Yoshida T, Eguchi K, Yoshe K, Kasuya S (1992) Japanese Patent JP 92-318266 321127 (Chem Abstr 121:208539)
Onoe J, Ooyama T, Takeuchi K (1992) Japanese Patent JP 92-231173 920831 (Chem Abstr 121:147754)
Kurita N, Kobayashi K, Kumado H, Tago K (1992) Japanese Patent JP 92-154720 920615 (ChemAbstr 120:221682)
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Hummelen, J.C., Bellavia-Lund, C., Wudl, F. (1999). Heterofullerenes. In: Hirsch, A. (eds) Fullerenes and Related Structures. Topics in Current Chemistry, vol 199. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-68117-5_3
Download citation
DOI: https://doi.org/10.1007/3-540-68117-5_3
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-64939-7
Online ISBN: 978-3-540-68117-5
eBook Packages: Springer Book Archive