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Coulombic-Enhanced Hetero Radical Pairing Interactions

Abstract:Spin-spin interactions between two identical aromatic radicals has been studied1extensively and utilized to establish supramolecular recognition. Here we report2that, spin-pairing interactions could also take place between two different π-electron radicals, namely a bipyridinium radical cation (BPY+?) and a naphthalene-1,8:4,5-bis(dicarboximide) radical anion (NDI─?). The occurrence of this type of previously unreported hetero radical pairing interactions is attributed to enhancement effect of Coulombic attraction between these two radicals bearing opposite charges. The Coulombic-enhanced hetero radical pairing interactions are employed to drive host-guest recognition, as well as the reversible switching of a bistable [2]rotaxane.


1.     Trabolsi, A.et al. Radically enhanced molecular recognition.Nat. Chem.2, 42-49 (2010).

2.     Zheng, X.et al. Coulombic-enhanced hetero radical pairing interactions.Nat. Commun. DOI: 10.1038/s41467-018-04335-0 (2018)


 Education and Working Experience

·       Tenure-track Professor

Department of Chemistry, Zhejiang University, China    2015–present

·       Postdoctoral Fellow

Department of Chemistry, the University of Texas at Austin, Austin, Texas, USA    2013–2015

·       PhD in Organic Chemistry

Department of Chemistry, Northwestern University, Evanston, Illinois, USA    2007–2012

·       MSc in Organic Chemistry

Department of Chemistry, Wuhan University, People’s Republic of China    2005–2007

·       BS in Chemistry

Department of Chemistry, Wuhan University, People’s Republic of China    2001–2005


Scholarships and Awards

·        Thousand Young Talents Plan                                                                                                                2015

·        The Chinese Government Award for Outstanding Self-Financed Student Abroad                     2012

  Publications(as the First Author)

  1. Zheng, X.; Zhang, Y.; Cao, N.; Li, X.; Zhang, S.; Du, R.; Wang, H.; Ye, Z.; Wang, Y.; Cao, F.; Li, H.; Hong, X.; Sue, A. C.-H.; Yang, C.; Liu, W.-G.;Li, H.“Coulombic-enhanced hetero radical pairing interactions.”Nature Commun.2018, DOI:DOI: 10.1038/s41467-018-04335-0.
  2. Wu, G.; Wang, C.-Y.; Jiao, T.; Zhu, H.; Huang, F.;Li, H.“Controllable Self-Assembly of Macrocycles in Water for Isolating Aromatic Hydrocarbon Isomers.”J. Am. Chem. Soc.2018,140,5955–5961.
  3. Jiao, T.; Chen, L.; Yang, D.; Li, X.; Wu, G.; Zeng, P.; Zhou, A.; Yin, Q.; Pan, Y.; Wu, B.; Hong, X.; Kong, X.; Lynch, V. M.; Sessler, J. L.;Li, H.“Trapping White Phosphorus within a Purely Organic Molecular Container Produced by Imine Condensation.”Angew. Chem. Int. Ed.2017,56, 14545–14550.
  4. Li, H.; Zhang, H.; Lammer, A. D.; Wang, M.; Li, X.; Lynch, V. M.; Sessler, J. L. “Quantitative Self-Assembly of A Purely Organic Three-Dimensional Catenane in Water.”Nature Chem.2015,7, 1003–1008.
  5. Li, H.; Cheng, C.; McGonigal, P. R.; Fahrenbach, A. C.; Frasconi, M.; Liu, W.-G.; Zhu, Z.; Zhao, Y.; Ke, C.; Lei, J.; Young, R. M.; Dyar, S. M.; Co, D. T.; Yang, Y.-W.; Botros, Y. Y.; Goddard, W. A. III; Wasielewski, M. R.; Astumian, R. D.; Stoddart, J. F. “Relative Unidirectional Translation in an Artificial Molecular Assembly Fueled by Light.”J. Am. Chem. Soc.2013,135,18609–18620.
  6. Jia, C.+;Li, H.+; Jiang, J.; Wang, J.; Chen, H.; Cao, D.; Stoddart, J. F. Guo, X. “Interface-engineered bistable [2]rotaxane-graphene hybrids with logic capabilities.”Adv. Mater.2013,25, 6752–6759.+Equal contribution. First author in Stoddart group.
  7. Li, H.; Zhu, Z.; Fahrenbach, A. C.; Savoie, B. M.; Ke, C.; Barnes, J. C.; Lei, J.; Zhao, Y.-L.; Lilley, L. M.; Marks, T. J.; Ratner, M. A.; Stoddart, J. F. “Mechanical Bond-Induced Radical Stabilization.”J. Am. Chem. Soc.2013,135,456–467.Highlighted Article.
  8. Zhu, Z.+;Li, H.+; Colquhoun, H. M.; Stoddart, J. F. “Oligomeric Pseudorotaxanes Adopting Infinite-Chain Lattice Superstructures.”Angew. Chem. Int. Ed.2012,51, 7231–7235.+Equal contribution.
  9. Avellini, T.+;Li, H.+; Coskun, A.+; Barin, G.; Trabolsi, A.; Basuray, A. N.; Dey, S. K.; Credi, A.; Silvi, S.; Stoddart, J. F.; Venturi, M. “Photoinduced Memory Effect in A Redox Controllable Bistable Mechanical Molecular Switch.”Angew. Chem. Int. Ed.2012, 51, 1611–1615.+Equal contribution. First author in Stoddart group.
  10. Li, H.; Fahrenbach, A. C.; Coskun, A.; Zhu, Z.; Barin, G.; Zhao, Y.-L.; Botros, Y. Y.; Sauvage, J.-P.; Stoddart, J. F. “A Light–Stimulated Molecular Switch Driven by Radical–Radical Interactions in Water.”Angew. Chem. Int. Ed.2011, 50, 6782–6788.
  11. Li, H.; Zhao, Y.-L.; Fahrenbach, A. C.; Kim, S.-Y.; Paxton, W. F.; Stoddart, J. F. “Degenerate [2]Rotaxanes with Electrostatic Barriers.”Org. Biomol. Chem.2011, 9, 2240–2250.Hot Paper.
  12. Li, H.; Fahrenbach, A. C.; Dey, S. K.; Basu, S.;Trabolsi, A.; Zhu, Z.; Botros, Y. Y.; Stoddart, J. F. “Mechanical Bond Formation by Radical Templation.” Angew. Chem. Int. Ed.2010, 49, 8260–8265.VIP Paper.



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