CC BY 4.0 · SynOpen 2024; 08(01): 91-99
DOI: 10.1055/a-2274-5102
letter

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

Sambasivarao Kotha
,
Deepshikha Singh


Abstract

We disclose a useful approach to novel tetrahedral building blocks containing N-heterocycles. Pyrrole was introduced on to the tetraphenylmethane (TPM) core by employing the RCM strategy, Clauson–Kaas reaction, Paal–Knorr condensation, and Ullmann coupling as key steps. In addition, various heterocyclic derivatives of TPM were prepared using nickel catalysts. We also studied the photophysical properties of the synthesized TPM derivatives containing different peripheral substituents and found that they exhibit high quantum yields.

Supporting Information



Publication History

Received: 30 November 2023

Accepted after revision: 26 January 2024

Accepted Manuscript online:
22 February 2024

Article published online:
26 March 2024

© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution 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/4.0/)

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  • References

  • 1 Bulumulla C, Gunawardhana R, Gamage PL, Miller JT, Kularatne RN, Biewer MC, Stefan MC. ACS Appl. Mater. Interfaces 2020; 29: 32209
  • 2 Zhang X, Richter LJ, DeLongchamp DM, Kline RJ, Hammond MR, McCulloch I, Heeney M, Ashraf RS, Smith JN, Anthopoulos TD, Schroeder B, Geerts YH, Fischer DA, Toney MF. J. Am. Chem. Soc. 2011; 133: 15073
  • 3 Howard JK, Rihak KJ, Hyland CJ. T, Bissember AC, Smith JA. Org. Biomol. Chem. 2016; 14: 8873
  • 4 Qiao Y, Zhang J, Xu W, Zhu D. J. Mater. Chem. 2012; 22: 5706
    • 5a Han X, Huang J, Yuan C, Liu Y, Cui Y. J. Am. Chem. Soc. 2018; 140: 892
    • 5b Liu X, Shi X, Liu C, Ren Y, Wu Y, Yang W, Alsaedi A, Hayat T, Kong F, Liu X, Ding Y, Yao J, Dai S. J. Phys. Chem. C 2018; 122: 26337
  • 6 Thomas JM. H, Trewin A. J. Phys. Chem. C 2014; 118: 19712
  • 7 Zaręba JK. Inorg. Chem. Commun. 2017; 86: 172
  • 8 Li X, Yu Y, Liu Q, Meng Y. ACS Appl. Mater. Interfaces 2012; 4: 3627
  • 9 Liu XM, He C, Huang J, Xu J. Chem. Mater. 2005; 17: 434
  • 10 Bai D.-R, Wang S. Organometallics 2004; 23: 5958
    • 11a Ma L, Jin A, Xie Z, Lin W. Angew. Chem. Int. Ed. 2009; 48: 9905
    • 11b Sengupta S, Sadhukhan SK. Tetrahedron Lett. 1999; 40: 9157
  • 12 Uribe-Romo FJ, Hunt JR, Furukawa H, Klock C, O’keeffe M, Yagh OM. J. Am. Chem. Soc. 2009; 131: 4570
  • 13 Pop L, Golban ML, Hadade ND, Socaci C, Grosu I. Synthesis 2015; 47: 2799
  • 14 Zaręba JK, Białek MJ, Janczak J, Zoń J, Dobosz A. Cryst. Growth Des. 2014; 14: 6143
  • 15 Bauer T, Schlüter AD, Sakamoto J. Synlett 2010; 877
  • 16 Mao H, Zhang S. J. Mater. Chem. A 2014; 2: 9835
  • 17 Astruc D, Boisselier E, Ornelas C. Chem. Rev. 2010; 110: 1857
    • 18a Hu X, Wang H, Faul CF. J, Wen J, Wei Y, Zhu M, Liao Y. Chem. Eng. J. 2020; 382: 122998
    • 18b Lau CH, Konstas K, Doherty CM, Kanehashi S, Ozcelik B, Kentish SE, Hill AJ, Hill MR. Chem. Mater. 2015; 27: 4756
  • 19 Valášek M, Lindner M, Mayo M. Beilstein J. Nanotechnol. 2016; 7: 374
    • 20a Zimmermann TJ, Müller TJ. J. Synthesis 2002; 1157
    • 20b Sengupta S, Sadhukhan SK, Muhuri S. Synlett 2003; 2329
    • 20c Villa M, Ceroni P, Fermi A. ChemPlusChem 2022; 87: e202100558
  • 21 Rohit KR, Meera G, Anilkumar G. J. Heterocycl. Chem. 2022; 59: 194
  • 22 Kim BH, Bae S, Go A, Lee H, Gong C, Lee BM. Org. Biomol. Chem. 2016; 14: 265
  • 23 Varala R, Seema V, Dubasi N. Organics 2023; 4: 1
  • 24 Suresh P, Pitchumani K. J. Org. Chem. 2008; 73: 9121
  • 25 Zhu L, Guo P, Li G, Lan J, Xie R, You J. J. Org. Chem. 2007; 72: 8535
  • 26 Liu CZ, Wang JJ, Yang B, Li Z.-Y, Yan M, Liu X.-M, Hu Z.-Y, Liu L.-T, Li Z.-T. Chem. Commun. 2023; 59: 11580
    • 27a Kotha S, Ganesh T, Ghosh AK. Bioorg. Med. Chem. Lett. 2000; 10: 1755
    • 27b Kotha S, Sreenivasachary N. Bioorg. Med. Chem. Lett. 2000; 10: 1413
    • 27c Kotha S, Brahmachary E. Bioorg. Med. Chem. Lett. 2002; 10: 2291
    • 27d Kotha S, Singh K. Tetrahedron Lett. 2004; 45: 9607
    • 27e Kotha S, Manivannan E, Ganesh T, Sreenivasachary N, Deb A. Synlett 1999; 1621
    • 27f Kotha S, Enugurthi B. Bioorg. Med. Chem. Lett. 1997; 7: 2719
  • 28 Yeh C.-H, Lee R.-H, Chan LH, Lin T.-YJ, Chen C.-Ti, Balasubramaniam E, Tao YT. Chem. Mater. 2001; 13: 2788
  • 29 Laliberté D, Maris T, Wuest JD. Can. J. Chem. 2004; 82: 386