109
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Two-fold enhancement of equatorial bis-PCBM-C60 adducts using a supramolecular mask

, &
Received 26 Feb 2024, Accepted 26 Mar 2024, Published online: 04 Apr 2024

References

  • Lenes M, Wetzelaer G-JAH, Kooistra FB, et al. Fullerene bisadducts for enhanced open-circuit voltages and efficiencies in polymer solar cells. Adv Mater. 2008;20(11):2116–2119. doi: 10.1002/adma.200702438
  • Janssen RAJ, Hummelen JC, Wudl F. Photochemical fulleroid to methanofullerene conversion via the Di-.Pi.-methane (Zimmerman) rearrangement. J Am Chem Soc. 1995;117(1):544–545. doi: 10.1021/ja00106a068
  • Hummelen JC, Knight BW, LePeq F, et al. Preparation and characterization of Fulleroid and methanofullerene derivatives. J Org Chem. 1995;60(3):532–538. doi: 10.1021/jo00108a012
  • Fuertes-Espinosa C, García-Simón C, Pujals M, et al. Supramolecular fullerene sponges as catalytic masks for regioselective functionalization of C60. Chem. 2020;6(1):169–186. doi: 10.1016/j.chempr.2019.10.010
  • Pujals M, Pèlachs T, Fuertes-Espinosa C, et al. Regioselective access to orthogonal Diels-Alder C60 bis-adducts and tris-heteroadducts via supramolecular mask strategy. Cell Rep Phys Sci. 2022;3(8):100992. doi: 10.1016/j.xcrp.2022.100992
  • Liu T, Abrahams I, Dennis TJS. Structural identification of 19 purified isomers of the OPV acceptor material bisPCBM by 13C NMR and UV–vis absorption spectroscopy and high-performance liquid chromatography. J Phys Chem A. 2018;122(16):4138–4152. doi: 10.1021/acs.jpca.8b00713
  • Hirsch A, Lamparth I, Karfunkel HR. Fullerene chemistry in three dimensions: isolation of seven regioisomeric bisadducts and chiral trisadducts of C60 and Di(ethoxycarbonyl)methylene. Angew Chem Int Ed Engl. 1994;33(4):437–438. doi: 10.1002/anie.199404371
  • García-Simón C, Garcia-Borràs M, Gómez L, et al. Sponge-like molecular cage for purification of fullerenes. Nat Commun. 2014;5:5557. doi: 10.1038/ncomms6557
  • Bingel C. Cyclopropanierung von Fullerenen. Chem Ber. 1993;126(8):1957–1959. doi: 10.1002/cber.19931260829
  • Iannace V, Sabrià C, Xu Y, et al. Regioswitchable bingel bis-functionalization of fullerene C70 via supramolecular masks. J Am Chem Soc. 2024;146(8):5186–5194. doi: 10.1021/jacs.3c10808
  • Fuertes-Espinosa C, Pujals M, Ribas X. Supramolecular purification and regioselective functionalization of fullerenes and endohedral metallofullerenes. Chem. 2020;6(12):3219–3262. doi: 10.1016/j.chempr.2020.11.003
  • Ubasart E, Borodin O, Fuertes-Espinosa C, et al. A three-shell supramolecular complex enables the symmetry-mismatched chemo- and regioselective bis-functionalization of C60. Nat Chem. 2021;13(5):420–427. doi: 10.1038/s41557-021-00658-6
  • Wang Y, Cao J, Schuster DI, et al. A superior synthesis of [6,6]-methanofullerenes: the reaction of sulfonium ylides with C60. Tetrahedron Lett. 1995;36(38):6843–6846. doi: 10.1016/0040-4039(95)01443-L
  • Ito H, Kishi Y, Nishikawa Y, et al. A general method for the synthesis of 2,2-[60]fullerenoalkanals: the reaction of [60]fullerene with 2-bromoenol silyl ethers. Synlett. 2010;2010(12):1811–1814. doi: 10.1055/s-0030-1258112
  • Ito T, Iwai T, Matsumoto F, et al. Facile synthesis of [6,6]-phenyl-C61/71-butyric acid methyl esters via sulfur ylides for bulk-heterojunction solar cell. Synlett. 2013;24(15):1988–1992. doi: 10.1055/s-0033-1339481
  • Shi W, Hou X, Liu T, et al. Purification and electronic characterisation of 18 isomers of the OPV acceptor material bis-[60]PCBM. Chem Commun. 2017;53(5):975–978. doi: 10.1039/C6CC07820F

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.