Skip to main content
Log in

A Long Pathway to the Quantitative Assembly of Metallodendrimers

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

This overview describes our research progression from the study of heterocycle synthesis to dendritic architecture to simple metallomacrocycles, and finally to complex, fractal-based, suprametallomolecular materials. Construction of the first terpyridine-modified dendritic scaffold was followed by the construction and self-assembly of polyterpyridine monomers. Preparation of tristerpyridine building blocks used in concert with bisterpyridine analogs facilitated access to a Sierpiński gasket, as verified by direct visual observation with UHV-STEM, as well as other techniques. Numerous examples of heteroleptic self-assembly are described that include the quantitative preparation of a Sierpiński triangle. Addition of angled spacer moieties within polyterpyridine building blocks has generated a new family of 3D spherical materials that has facilitated the construction of hybrid fractal-dendritic materials that exhibit the unexpected concentration mediated, architectural transformations.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Scheme 2
Scheme 3
Fig. 2
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9

Similar content being viewed by others

References

  1. T. Anderson, Earth Environ. Trans. R. Soc. Edinb. 16, 123 (1846)

    Article  Google Scholar 

  2. F. Blau, Ber. Dtsch. Chem. Ges. 21, 1077 (1888)

    Article  Google Scholar 

  3. G.T. Morgan, F.H. Burstall, J. Chem. Soc. 20 (1932)

  4. G.T. Morgan, F.H. Burstall, J. Chem. Soc. 1649 (1937)

  5. D.L. Fishel, G.R. Newkome, J. Am. Chem. Soc. 88, 3654 (1966)

    Article  CAS  Google Scholar 

  6. G.R. Newkome, D.L. Fishel, J. Org. Chem. 37, 1329 (1972)

    Article  CAS  Google Scholar 

  7. F. Kröhnke, Synthesis 1976, 1 (1976)

    Article  Google Scholar 

  8. E. Buhleier, W. Wehner, F. Vögtle, Synthesis 9, 155 (1978)

    Article  Google Scholar 

  9. D.A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, P. Smith, Polym. J. 17, 117 (1985)

    Article  CAS  Google Scholar 

  10. G.R. Newkome, Z.-q. Yao, G.R. Baker, V.K. Gupta, J. Org. Chem. 50, 2003 (1985)

    Article  CAS  Google Scholar 

  11. W. Worthy, Chem. Eng. News 66, 19 (1988)

    Article  Google Scholar 

  12. F.M. Menger, Top. Curr. Chem. 136, 1 (1986)

    Article  CAS  Google Scholar 

  13. https://en.wikipedia.org/wiki/Biomimetics

  14. J.R. Lloyd, P.S. Jayasekara, K.A. Jacobson, Anal. Methods 8, 263 (2016)

    Article  CAS  Google Scholar 

  15. C.J. Hawker, J.M.J. Fréchet, J. Am. Chem. Soc. 112, 7638 (1990)

    Article  CAS  Google Scholar 

  16. H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2005 (2001)

    Google Scholar 

  17. J. Ruiz, G. Lafuente, S. Marcen, C. Ornelas, S. Lazare, E. Cloutet, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 125, 7250 (2003)

    Article  CAS  Google Scholar 

  18. G.R. Newkome, F. Cardullo, E.C. Constable, C.N. Moorefield, A.M.W.C. Thompson, J. Chem. Soc. Chem. Commun. 11, 925 (1993)

    Article  Google Scholar 

  19. G.R. Newkome, R. Güther, C.N. Moorefield, F. Cardullo, L. Echegoyen, E. Pérez-Cordero, H. Luftmann, Angew. Chem., Int. Ed. Engl. 34, 2023 (1995)

    Article  CAS  Google Scholar 

  20. G.R. Newkome, T.J. Cho, C.N. Moorefield, G.R. Baker, M.J. Saunders, R. Cush, P.S. Russo, Angew. Chem. Int. Ed. 38, 3717 (1999)

    Article  CAS  Google Scholar 

  21. G.R. Newkome, T.J. Cho, C.N. Moorefield, R. Cush, P.S. Russo, L.A. Godínez, M.J. Saunders, P. Mohapatra, Chem. Eur. J. 8, 2946 (2002)

    Article  CAS  Google Scholar 

  22. P. Wang, C.N. Moorefield, K.-U. Jeong, S.-H. Hwang, S. Li, S.Z.D. Cheng, G.R. Newkome, Adv. Mater. 20, 1381 (2008)

    Article  CAS  Google Scholar 

  23. G.R. Newkome, P. Wang, C.N. Moorefield, T.J. Cho, P. Mohapatra, S. Li, S.-H. Hwang, O. Lukoyanova, L. Echegoyen, J.A. Palagallo, V. Iancu, S.-W. Hla, Science 312, 1782 (2006)

    Article  CAS  Google Scholar 

  24. X. Lu, X. Li, J.-L. Wang, C.N. Moorefield, C. Wesdemiotis, G.R. Newkome, Chem. Commun. 48, 9873 (2012)

    Article  CAS  Google Scholar 

  25. D. Liu, Z. Jiang, M. Wang, X. Yang, H. Liu, M. Chen, C.N. Moorefield, G.R. Newkome, X. Li, P. Wang, Chem. Commun. 52, 9773 (2016)

    Article  CAS  Google Scholar 

  26. J.M. Ludlow, III, T.-Z. Xie, Z. Guo, K. Guo, M.J. Saunders, C.N. Moorefield, C. Wesdemiotis, G.R. Newkome, Chem. Commun. 51, 3820 (2015)

    Article  CAS  Google Scholar 

  27. J.M. Ludlow III, M.J. Saunders, M. Huang, Z. Guo, C.N. Moorefield, S.Z.D. Cheng, C. Wesdemiotis, G.R. Newkome, Supramol. Chem. 29, 69 (2017)

    Article  CAS  Google Scholar 

  28. R. Sarkar, K. Guo, C.N. Moorefield, M.J. Saunders, C. Wesdemiotis, G.R. Newkome, Angew. Chem. Int. Ed. 53, 12182 (2014)

    Article  CAS  Google Scholar 

  29. Z. Jiang, Y. Li, M. Wang, D. Liu, J. Yuan, M. Chen, J. Wang, G.R. Newkome, W. Sun, X. Li, P. Wang, Angew. Chem. Int. Ed. 56, 11450 (2017)

    Article  CAS  Google Scholar 

  30. Z. Jiang, Y. Li, M. Wang, B. Song, K. Wang, M. Sun, D. Liu, X. Li, J. Yuan, M. Chen, Y. Guo, X. Yang, T. Zhang, C.N. Moorefield, G.R. Newkome, B. Xu, X. Li, P. Wang, Nat. Commun. 8, 1 (2017)

    Article  Google Scholar 

  31. T.-Z. Xie, S.-Y. Liao, K. Guo, X. Lu, X. Dong, M. Huang, C.N. Moorefield, S.Z.D. Cheng, X. Liu, C. Wesdemiotis, G.R. Newkome, J. Am. Chem. Soc. 136, 8165 (2014)

    Article  CAS  Google Scholar 

  32. S. Chakraborty, W. Hong, K.J. Endres, T.-Z. Xie, L. Wojtas, C.N. Moorefield, C. Wesdemiotis, G.R. Newkome, J. Am. Chem. Soc. 139, 3012 (2017)

    Article  CAS  Google Scholar 

  33. Y. Yao, S. Chakraborty, S. Zhu, K.J. Endres, T.-Z. Xie, W. Hong, E. Manandhar, C.N. Moorefield, C. Wesdemiotis, G.R. Newkome, Chem. Commun. 53, 8038 (2017)

    Article  CAS  Google Scholar 

  34. M. Chen, J. Wang, D. Liu, Z. Jiang, Q. Liu, X. Yang, W. Yu, J. Yan, G.R. Newkome, P. Wang, Chem. Commun. (2017). doi:10.1039/C7CC05577C

    Google Scholar 

  35. T.-Z. Xie, K. Guo, Z. Guo, W.-Y. Gao, L. Wojtas, G.-H. Ning, M. Huang, X. Lu, J.-Y. Li, S.-Y. Liao, Y.-S. Chen, C.N. Moorefield, M.J. Saunders, S.Z.D. Cheng, C. Wesdemiotis, G.R. Newkome, Angew. Chem. Int. Ed. 54, 9224 (2015)

    Article  CAS  Google Scholar 

  36. T.-Z. Xie, K.J. Endres, Z. Guo, J.M. Ludlow III, C.N. Moorefield, M.J. Saunders, C. Wesdemiotis, G.R. Newkome, J. Am. Chem. Soc. 138, 12344 (2016)

    Article  CAS  Google Scholar 

  37. S. Chakraborty, R. Sarkar, K. Endres, T.-Z. Xie, M. Ghosh, C.N. Moorefield, M.J. Saunders, C. Wesdemiotis, G.R. Newkome, Eur. J. Org. Chem. 5091 (2016)

  38. T. Wu, Y.S. Chen, M. Chen, Q. Liu, X. Xue, Y. Shen, J. Wang, H. Huang, Y.T. Chan, P. Wang, Inorg. Chem. 56, 4065 (2017)

    Article  CAS  Google Scholar 

  39. G.R. Newkome, C.N. Moorefield, et al., US Pat. Applied, 2015

  40. G.R. Newkome, C.N. Moorefield, G.R. Baker, M.J. Saunders, S.H. Grossman, Angew. Chem. Int. Ed. Engl. 30, 1178 (1991)

    Article  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the funding from the National Science Foundation (CHE-1151991), the James and Vanita Oelschlager funding via the University of Akron, and the numerous undergraduate and graduate students, postdoctoral fellows, and visiting faculty, who were part of this adventure.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to George R. Newkome.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Newkome, G.R., Moorefield, C.N. & Chakraborty, S. A Long Pathway to the Quantitative Assembly of Metallodendrimers. J Inorg Organomet Polym 28, 360–368 (2018). https://doi.org/10.1007/s10904-017-0676-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-017-0676-8

Keywords

Navigation