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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 146-154
DOI: 10.1055/s-0041-1727182
Focus Issue: Peter Bäuerle 65th Birthday
Short Review

Supramolecular Approaches for Taming the Chemo- and Regiochemistry of C60 Addition Reactions

Sebastian B. Beil 
a   Institute of Organic Chemistry, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
b   Current address: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States
,
Max von Delius 
a   Institute of Organic Chemistry, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
› Author Affiliations Funding Information We are grateful for financial support from the Deutsche Forschungsgemeinschaft (DFG, 182849149-SFB953, 364549901–TRR 234, DE1830/1, DE1830/5), the European Research Council (ERCstg 802428 SUPRANET) and the University of Ulm.
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Abstract

The chemo- and regioselective functionalization of fullerenes is a long-standing problem of organic synthesis. Over the past five years, this fundamental challenge has gained technological relevance, because studies on single bis-adduct isomers in new-generation solar cells have demonstrated that the widespread use of isomer mixtures leads to suboptimal power conversion efficiencies. Herein, we review recent work on supramolecular approaches for achieving chemo- and regioselective syntheses of multiply functionalized derivatives of C60.

Key words

fullerenes - template effect - supramolecular chemistry - regioselectivity - organic photovoltaics - host–guest chemistry

Dedicated to Prof. Peter Bäuerle on the occasion of his 65th birthday.




Publication History

Received: 15 January 2021

Accepted: 09 February 2021

Article published online:
01 April 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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  • References

    • 1a Krätschmer W, Lamb LD, Fostiropoulos K, Huffman DR. Nature 1990; 347: 354
      CrossrefPubMed
    • 1b Krätschmer W. Nanoscale 2011; 3: 2485
      CrossrefPubMed
  • 3 Puente Santiago AR, Fernandez-Delgado O, Gomez A, Ahsan MA, Echegoyen L. Angew. Chem. Int. Ed. 2021; 60: 122
    CrossrefPubMed
  • 4 Maggini M, Scorrano G, Prato M. J. Am. Chem. Soc. 1993; 115: 9798
    CrossrefPubMed
    • 6a Hirsch A, Lamparth I, Karfunkel HR. Angew. Chem. Int. Ed. Engl. 1994; 33: 437
      CrossrefPubMed
    • 6b Djojo F, Herzog A, Lamparth I, Hampel F, Hirsch A. Chem. Eur. J. 1996; 2: 1537
      CrossrefPubMed
    • 6c Hirsch A, Lamparth I, Groesser T, Karfunkel HR. J. Am. Chem. Soc. 1994; 116: 9385
      CrossrefPubMed
    • 7a Suzuki T, Li Q, Khemani KC, Wudl F, Almarsson O. Science 1991; 254: 1186
      CrossrefPubMed
    • 7b Hummelen JC, Knight BW, LePeq F, Wudl F, Yao J, Wilkins CL. J. Org. Chem. 1995; 60: 532
      CrossrefPubMed
  • 8 Umeyama T, Imahori H. Acc. Chem. Res. 2019; 52: 2046
    CrossrefPubMed
  • 9 He Y, Chen H.-Y, Hou J, Li Y. J. Am. Chem. Soc. 2010; 132: 1377
    CrossrefPubMed
    • 10a Yan C, Barlow S, Wang Z, Yan H, Jen AK. Y, Marder SR, Zhan X. Nat. Rev. Mater. 2018; 3: 18003
      CrossrefPubMed
    • 10b Cheng P, Li G, Zhan X, Yang Y. Nat. Photonics 2018; 12: 131
      CrossrefPubMed
    • 10c Yu Z.-P, Liu Z.-X, Chen F.-X, Qin R, Lau T.-K, Yin J.-L, Kong X, Lu X, Shi M, Li C.-Z, Chen H. Nat. Commun. 2019; 10: 2152
      CrossrefPubMed
    • 10d Hou J, Inganäs O, Friend RH, Gao F. Nat. Mater. 2018; 17: 119
      CrossrefPubMed
    • 10e Nian L, Kan Y, Gao K, Zhang M, Li N, Zhou G, Jo SB, Shi X, Lin F, Rong Q, Liu F, Zhou G, Jen AK. Y. Joule 2020; 4: 2223
      CrossrefPubMed
    • 10f Yuan J, Zhang Y, Zhou L, Zhang G, Yip H.-L, Lau T.-K, Lu X, Zhu C, Peng H, Johnson PA, Leclerc M, Cao Y, Ulanski J, Li Y, Zou Y. Joule 2019; 3: 1140
      CrossrefPubMed
    • 10g Yao J, Qiu B, Zhang Z.-G, Xue L, Wang R, Zhang C, Chen S, Zhou Q, Sun C, Yang C, Xiao M, Meng L, Li Y. Nat. Commun. 2020; 11: 2726
      CrossrefPubMed
    • 10h Cui Y, Yao H, Zhang J, Zhang T, Wang Y, Hong L, Xian K, Xu B, Zhang S, Peng J, Wei Z, Gao F, Hou J. Nat. Commun. 2019; 10: 2515
      CrossrefPubMed
  • 11 Fuertes-Espinosa C, Pujals M, Ribas X. Chem 2020; 6: 3219
    CrossrefPubMed
  • 12 Berger PR, Kim M. J. Renewable Sustainable Energy 2018; 10: 013508
    CrossrefPubMed
    • 13a Anthopoulos TD, Tanase C, Setayesh S, Meijer EJ, Hummelen JC, Blom PW. M, de Leeuw DM. Adv. Mater. 2004; 16: 2174
      CrossrefPubMed
    • 13b Dodabalapur A, Katz HE, Torsi L, Haddon RC. Science 1995; 269: 1560
      CrossrefPubMed
    • 13c Haddon RC, Perel AS, Morris RC, Palstra TT. M, Hebard AF, Fleming RM. Appl. Phys. Lett. 1995; 67: 121
      CrossrefPubMed
    • 13d Dodabalapur A, Katz HE, Torsi L, Haddon RC. Appl. Phys. Lett. 1996; 68: 1108
      CrossrefPubMed
    • 13e Meijer EJ, de Leeuw DM, Setayesh S, van Veenendaal E, Huisman BH, Blom PW. M, Hummelen JC, Scherf U, Kadam J, Klapwijk TM. Nat. Mater. 2003; 2: 678
      CrossrefPubMed
    • 13f Newman CR, Frisbie CD, da Silva Filho DA, Brédas J.-L, Ewbank PC, Mann KR. Chem. Mater. 2004; 16: 4436
      CrossrefPubMed
  • 14 He Y, Li Y. Phys. Chem. Chem. Phys. 2011; 13: 1970
    CrossrefPubMed
    • 15a Zhao J, Li Y, Yang G, Jiang K, Lin H, Ade H, Ma W, Yan H. Nat. Energy 2016; 1: 15027
      PubMed
    • 15b Liu Y, Zhao J, Li Z, Mu C, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H. Nat. Commun. 2014; 5: 5293
      CrossrefPubMed
  • 16 Meng L, Zhang Y, Wan X, Li C, Zhang X, Wang Y, Ke X, Xiao Z, Ding L, Xia R, Yip H.-L, Cao Y, Chen Y. Science 2018; 361: 1094
    CrossrefPubMed
  • 17 Kim Y, Cho C.-H, Kang H, Kim K.-H, Park S, Kang TE, Park K, Kim BJ. Sol. Energy Mater. Sol. Cells 2015; 141: 87
    CrossrefPubMed
    • 18a Lenes M, Wetzelaer G.-J. A. H, Kooistra FB, Veenstra SC, Hummelen JC, Blom PW. M. Adv. Mater. 2008; 20: 2116
      CrossrefPubMed
    • 18b Li Y. Chem. Asian J. 2013; 8: 2316
      CrossrefPubMed
    • 18c Deng L.-L, Xie S.-Y, Gao F. Adv. Electron. Mater. 2018; 4: 1700435
      CrossrefPubMed
    • 18d Li Y. Acc. Chem. Res. 2012; 45: 723
      CrossrefPubMed
    • 18e Castro E, Murillo J, Fernandez-Delgado O, Echegoyen L. J. Mater. Chem. C 2018; 6: 2635
      CrossrefPubMed
    • 18f Lai Y.-Y, Cheng Y.-J, Hsu C.-S. Energy Environ. Sci. 2014; 7: 1866
      CrossrefPubMed
    • 19a Gadisa A, Svensson M, Andersson MR, Inganäs O. Appl. Phys. Lett. 2004; 84: 1609
      CrossrefPubMed
    • 19b Hoppe H, Egbe DA. M, Mühlbacher D, Sariciftci NS. J. Mater. Chem. 2004; 14: 3462
      CrossrefPubMed
    • 19c Scharber MC, Mühlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CJ. Adv. Mater. 2006; 18: 789
      CrossrefPubMed
    • 19d Morvillo P, Bobeico E. Sol. Energy Mater. Sol. Cells 2008; 92: 1192
      CrossrefPubMed
  • 20 Janssen RA. J, Nelson J. Adv. Mater. 2013; 25: 1847
    CrossrefPubMed
    • 21a Coakley KM, McGehee MD. Chem. Mater. 2004; 16: 4533
      CrossrefPubMed
    • 21b Li G, Shrotriya V, Huang J, Yao Y, Moriarty T, Emery K, Yang Y. Nat. Mater. 2005; 4: 864
      CrossrefPubMed
    • 21c Ball JM, Bouwer RK. M, Kooistra FB, Frost JM, Qi Y, Domingo EB, Smith J, Leeuw DM. d, Hummelen JC, Nelson J, Kahn A, Stingelin N, Bradley DD. C, Anthopoulos TD. J. Appl. Phys. 2011; 110: 014506
      PubMed
    • 22a Distler A, Sauermann T, Egelhaaf H.-J, Rodman S, Waller D, Cheon K.-S, Lee M, Guldi DM. Adv. Energy Mater. 2014; 4: 1300693
      CrossrefPubMed
    • 22b Heumueller T, Mateker WR, Distler A, Fritze UF, Cheacharoen R, Nguyen WH, Biele M, Salvador M, von Delius M, Egelhaaf H.-J, McGehee MD, Brabec CJ. Energy Environ. Sci. 2016; 9: 247
      CrossrefPubMed
  • 23 Wang CI, Hua CC. J. Phys. Chem. B 2015; 119: 14496
    CrossrefPubMed
  • 24 Cao T, Chen N, Liu G, Wan Y, Perea JD, Xia Y, Wang Z, Song B, Li N, Li X, Zhou Y, Brabec CJ, Li Y. J. Mater. Chem. A 2017; 5: 10206
    CrossrefPubMed
    • 25a Kitaura S, Kurotobi K, Sato M, Takano Y, Umeyama T, Imahori H. Chem. Commun. 2012; 48: 8550
      CrossrefPubMed
    • 25b Meng X, Zhao G, Xu Q, Tan Za, Zhang Z, Jiang L, Shu C, Wang C, Li Y. Adv. Funct. Mater. 2014; 24: 158
      CrossrefPubMed
    • 25c Tao R, Umeyama T, Kurotobi K, Imahori H. ACS Appl. Mater. Interfaces 2014; 6: 17313
      CrossrefPubMed
    • 26a Sabirov DS. J. Phys. Chem. C 2013; 117: 9148
      CrossrefPubMed
    • 26b Bouwer RK. M, Wetzelaer G.-J. A. H, Blom PW. M, Hummelen JC. J. Mater. Chem. 2012; 22: 15412
      CrossrefPubMed
    • 26c Liao M.-H, Lai Y.-Y, Lai Y.-Y, Chen Y.-T, Tsai C.-E, Liang W.-W, Cheng Y.-J. ACS Appl. Mater. Interfaces 2014; 6: 996
      CrossrefPubMed
    • 26d Cerón MR, Izquierdo M, Aghabali A, Valdez JA, Ghiassi KB, Olmstead MM, Balch AL, Wudl F, Echegoyen L. J. Am. Chem. Soc. 2015; 137: 7502
      CrossrefPubMed
  • 27 Shi W, Hou X, Liu T, Zhao X, Sieval AB, Hummelen JC, Dennis TJ. S. Chem. Commun. 2017; 53: 975
    CrossrefPubMed
  • 28 Lin Y, Chen B, Zhao F, Zheng X, Deng Y, Shao Y, Fang Y, Bai Y, Wang C, Huang J. Adv. Mater. 2017; 29: 1700607
    CrossrefPubMed
  • 29 Zhang F, Shi W, Luo J, Pellet N, Yi C, Li X, Zhao X, Dennis TJ. S, Li X, Wang S, Xiao Y, Zakeeruddin SM, Bi D, Grätzel M. Adv. Mater. 2017; 29: 1606806
    CrossrefPubMed
  • 30 Zhao F, Meng X, Feng Y, Jin Z, Zhou Q, Li H, Jiang L, Wang J, Li Y, Wang C. J. Mater. Chem. A 2015; 3: 14991
    CrossrefPubMed
    • 31a Dai S.-M, Zhang X, Chen W.-Y, Li X, Tan Za, Li C, Deng L.-L, Zhan X.-X, Lin M.-S, Xing Z, Wen T, Ho R.-M, Xie S.-Y, Huang R.-B, Zheng L.-S. J. Mater. Chem. A 2016; 4: 18776
      CrossrefPubMed
    • 31b Herrmann A, Rüttimann M, Thilgen C, Diederich F. Helv. Chim. Acta 1995; 78: 1673
      CrossrefPubMed
    • 31c Guo X, Cui C, Zhang M, Huo L, Huang Y, Hou J, Li Y. Energy Environ. Sci. 2012; 5: 7943
      CrossrefPubMed
    • 31d Kutsarov DI, Rašović I, Zachariadis A, Laskarakis A, Lebedeva MA, Porfyrakis K, Mills CA, Beliatis MJ, Fisher B, Bruchlos K, Ludwigs S, Logothetidis S, Silva SR. P. Adv. Electron. Mater. 2016; 2: 1600362
      CrossrefPubMed
    • 31e Wong WW. H, Subbiah J, White JM, Seyler H, Zhang B, Jones DJ, Holmes AB. Chem. Mater. 2014; 26: 1686
      CrossrefPubMed
    • 31f Tao R, Umeyama T, Higashino T, Koganezawa T, Imahori H. ACS Appl. Mater. Interfaces 2015; 7: 16676
      CrossrefPubMed
    • 31g Umeyama T, Takahara S, Shibata S, Igarashi K, Higashino T, Mishima K, Yamashita K, Imahori H. RSC Adv. 2018; 8: 18316
      CrossrefPubMed
    • 31h Umeyama T, Miyata T, Jakowetz AC, Shibata S, Kurotobi K, Higashino T, Koganezawa T, Tsujimoto M, Gélinas S, Matsuda W, Seki S, Friend RH, Imahori H. Chem. Sci. 2017; 8: 181
      CrossrefPubMed
    • 31i Umeyama T, Shibata S, Miyata T, Igarashi K, Koganezawa T, Imahori H. RSC Adv 2017; 7: 45697
      CrossrefPubMed
    • 31j Umeyama T, Igarashi K, Sakamaki D, Seki S, Imahori H. Chem. Commun. 2018; 54: 405
      CrossrefPubMed
  • 32 Isaacs L, Haldimann RF, Diederich F. Angew. Chem. Int. Ed. Engl. 1994; 33: 2339
    CrossrefPubMed
    • 33a Kräutler B, Müller T, Maynollo J, Gruber K, Kratky C, Ochsenbein P, Schwarzenbach D, Bürgi H.-B. Angew. Chem. Int. Ed. Engl. 1996; 35: 1204
      CrossrefPubMed
    • 33b Isaacs L, Diederich F, Haldimann RF. Helv. Chim. Acta 1997; 80: 317
      PubMed
    • 33c Schwenninger R, Müller T, Kräutler B. J. Am. Chem. Soc. 1997; 119: 9317
      CrossrefPubMed
    • 33d Qian W, Rubin Y. J. Am. Chem. Soc. 2000; 122: 9564
      CrossrefPubMed
    • 33e Beuerle F, Chronakis N, Hirsch A. Chem. Commun. 2005; 29: 3676
      PubMed
    • 33f Beuerle F, Hirsch A. Chem. Eur. J. 2009; 15: 7434
      CrossrefPubMed
    • 33g Ortiz AL, Echegoyen L. J. Mater. Chem. 2011; 21: 1362
      CrossrefPubMed
    • 33h Hörmann F, Donaubauer W, Hampel F, Hirsch A. Chem. Eur. J. 2012; 18: 3329
      CrossrefPubMed
    • 33i Tao R, Umeyama T, Higashino T, Koganezawa T, Imahori H. Chem. Commun. 2015; 51: 8233
      CrossrefPubMed
  • 34 Xiao Z, Geng X, He D, Jia X, Ding L. Energy Environ. Sci. 2016; 9: 2114
    CrossrefPubMed
  • 35 Dannhäuser J, Donaubauer W, Hampel F, Reiher M, Le Guennic B, Corzilius B, Dinse K.-P, Hirsch A. Angew. Chem. Int. Ed. 2006; 45: 3368
    CrossrefPubMed
  • 36 We use the term Bingel reaction for reactions between fullerenes and bromo malonates [see ref. 5a] and the term Bingel
    PubMed
  • 37 Bottari G, Trukhina O, Kahnt A, Frunzi M, Murata Y, Rodríguez-Fortea A, Poblet JM, Guldi DM, Torres T. Angew. Chem. Int. Ed. 2016; 55: 11020
    CrossrefPubMed
  • 38 Đorđević L, Casimiro L, Demitri N, Baroncini M, Silvi S, Arcudi F, Credi A, Prato M. Angew. Chem. Int. Ed. 2021; 60: 313
    CrossrefPubMed
  • 39 Xu Y, Kaur R, Wang B, Minameyer MB, Gsänger S, Meyer B, Drewello T, Guldi DM, von Delius M. J. Am. Chem. Soc. 2018; 140: 13413
    CrossrefPubMed
    • 40a Iwamoto T, Watanabe Y, Sadahiro T, Haino T, Yamago S. Angew. Chem. Int. Ed. 2011; 50: 8342
      CrossrefPubMed
    • 40b Xia J, Bacon JW, Jasti R. Chem. Sci. 2012; 3: 3018
      CrossrefPubMed
    • 40c Xu Y, von Delius M. Angew. Chem. Int. Ed. 2020; 59: 559
      CrossrefPubMed
    • 41a Lewis SE. Chem. Soc. Rev. 2015; 44: 2221
      CrossrefPubMed
    • 41b Hermann M, Wassy D, Esser B. Author Manuscript, Accepted DOI: 10.1002/anie.202007024.
      CrossrefPubMed
    • 41c Patel VK, Kayahara E, Yamago S. Chem. Eur. J. 2015; 21: 5742
      CrossrefPubMed
    • 41d Griwatz JH, Wegner HA. Org. Mater. 2020; 2: 306
      PubMed
    • 41e Darzi ER, Hirst ES, Weber CD, Zakharov LN, Lonergan MC, Jasti R. ACS Cent. Sci. 2015; 1: 335
      CrossrefPubMed
    • 41f Frydrych R, Lis T, Bury W, Cybińska J, Stępień M. J. Am. Chem. Soc. 2020; 142: 15604
      CrossrefPubMed
    • 41g Chen M, Unikela KS, Ramalakshmi R, Li B, Darrigan C, Chrostowska A, Liu S.-Y. Angew. Chem. Int. Ed. 2021; 60: 1556
      CrossrefPubMed
    • 41h Tran-Van A.-F, Wegner HA. Beilstein J. Nanotechnol. 2014; 5: 1320
      CrossrefPubMed
    • 42a García-Simón C, Costas M, Ribas X. Chem. Soc. Rev. 2016; 45: 40
      CrossrefPubMed
    • 42b Tashiro K, Aida T. Chem. Soc. Rev. 2007; 36: 189
      CrossrefPubMed
    • 42c Markiewicz G, Jenczak A, Kołodziejski M, Holstein JJ, Sanders JK. M, Stefankiewicz AR. Nat. Commun. 2017; 8: 15109
      CrossrefPubMed
    • 42d Wood DM, Meng W, Ronson TK, Stefankiewicz AR, Sanders JK. M, Nitschke JR. Angew. Chem. Int. Ed. 2015; 54: 3988
      CrossrefPubMed
    • 42e Chen B, Horiuchi S, Holstein JJ, Tessarolo J, Clever GH. Chem. Eur. J. 2019; 25: 14921
      CrossrefPubMed
    • 42f Boyd PD. W, Reed CA. Acc. Chem. Res. 2005; 38: 235
      CrossrefPubMed
  • 43 Chen B, Holstein JJ, Horiuchi S, Hiller WG, Clever GH. J. Am. Chem. Soc. 2019; 141: 8907
    CrossrefPubMed
  • 44 García-Simón C, Garcia-Borràs M, Gómez L, Parella T, Osuna S, Juanhuix J, Imaz I, Maspoch D, Costas M, Ribas X. Nat. Commun. 2014; 5: 5557
    CrossrefPubMed
  • 45 Brenner W, Ronson TK, Nitschke JR. J. Am. Chem. Soc. 2017; 139: 75
    CrossrefPubMed
  • 46 Leonhardt V, Fimmel S, Krause A.-M, Beuerle F. Chem. Sci. 2020; 11: 8409
    CrossrefPubMed
  • 47 Fuertes-Espinosa C, García-Simón C, Pujals M, Garcia-Borràs M, Gómez L, Parella T, Juanhuix J, Imaz I, Maspoch D, Costas M, Ribas X. Chem 2020; 6: 169
    PubMed
  • 48 Hasegawa S, Clever GH. Chem 2020; 6: 5
    CrossrefPubMed
  • 49 Ubasart E, Borodin O, Fuertes-Espinosa C, Xu Y, García-Simón C, Gómez L, Juanhuix J, Gándara F, Imaz I, Maspoch D, von Delius M, Ribas X. Nat. Chem. 2021; , In press DOI: 10.1038/s41557-021-00658-6.
    CrossrefPubMed