Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

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.

Key words

aryl iodide - heterocycles - aromatization - tetraphenylmethane - cross-coupling

Publikationsverlauf

Eingereicht: 30. November 2023

Angenommen nach Revision: 26. Januar 2024

Accepted Manuscript online:
22. Februar 2024

Artikel online veröffentlicht:
26. März 2024

• 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