Synthesis and Optical Resolution of Inherently Chiral Fluorescent Calix[4]arenes and Their Application in Chiral Recognition

This paper is dedicated to Prof. Guoqiang Lin on the occasion of his 80^th birthday, for his great contribution to organic chemistry in China.

Abstract

Inherently chiral calix[4]arenes were separated by condensation with chiral auxiliary (S)- and (R)-1-phenylethylamine using column chromatography on silica gel; subsequent derivatization with click chemistry furnished compounds with fluorescent properties that can be used for chiral recognition.

Key words

calix[4]arene - inherently chiral - click chemistry - fluorescent sensors - chiral resolution

Publication History

Received: 24 March 2023

Accepted after revision: 24 April 2023

Article published online:
24 May 2023

• References

• 1 No KH, Gutsche CD. J. Org. Chem. 1982; 47: 2713
• 2 Böhmer V, Kraft D, Tabatabai M. J. Inclusion Phenom. Mol. Recognit. Chem. 1994; 19: 17
• 3 Cort AD, Mandolini L, Pasquini C, Schiaffino L. New J. Chem. 2004; 28: 1198
• 4a Szumna A. Chem. Soc. Rev. 2010; 39: 4274
• 4b Wierzbicki M, Jedrzejewska H, Szumna A. In Calixarenes and Beyond . Neri P, Sessler JL, Wang M.-X. Springer; Cham: 2016: 13
• 5a Cao Y.-D, Luo J, Zheng Q.-Y, Chen C.-F, Wang M.-X, Huang Z.-T. J. Org. Chem. 2004; 69: 206
• 5b Luo J, Zheng Q.-Y, Chen C.-F, Huang Z.-T. Chem. Eur. J. 2005; 11: 5917
• 5c Luo J, Zheng Q.-Y, Chen C.-F, Huang Z.-T. Tetrahedron 2005; 61: 8517
• 5d Miao R, Zheng Q.-Y, Chen C.-F, Huang Z.-T. J. Org. Chem. 2005; 70: 7662
• 5e Xu Z.-X, Zhang C, Zheng Q.-Y, Chen C.-F, Huang Z.-T. Org. Lett. 2007; 9: 4447
• 5f Xu Z.-X, Li G.-K, Chen C.-F, Huang Z.-T. Tetrahedron 2008; 64: 8668
• 5g Xu Z.-X, Zhang C, Yang Y, Chen C.-F, Huang Z.-T. Org. Lett. 2008; 10: 477
• 5h Xu ZX, Zhang C, Huang ZT, Chen CF. Chin. Sci. Bull. 2010; 55: 2859
• 6a Shirakawa S, Moriyama A, Shimizu S. Org. Lett. 2007; 9: 3117
• 6b Shirakawa S, Moriyama A, Shimizu S. Eur. J. Org. Chem. 2008; 5957
• 6c Shirakawa S, Kimura T, Murata S, Shimizu S. J. Org. Chem. 2009; 74: 1288
• 6d Shirakawa S, Shimizu S. Eur. J. Org. Chem. 2009; 1916
• 6e Shirakawa S, Shimizu S. New J. Chem. 2010; 34: 1217
• 7a Yakovenko V, Boyko VI, Danylyuk O, Suwinska K, Lipkowski J, Kalchenko VI. Org. Lett. 2007; 9: 1183
• 7b Boyko VI, Yakovenko AV, Matvieiev YI, Kalchenko OI, Shishkin OV, Shishkina SV, Kalchenko VI. Tetrahedron 2008; 64: 7567
• 7c Boyko VI, Matvieiev YI, Klyachina MA, Yesypenko OA, Shishkina SV, Shishkin OV, Kalchenko VI. Tetrahedron 2009; 65: 4220
• 8a Herbert SA, Arnott GE. Org. Lett. 2009; 11: 4986
• 8b Herbert SA, Arnott GE. Org. Lett. 2010; 12: 4600
• 8c Arnott GE. Chem. Eur. J. 2018; 24: 1744
• 9a Troisi F, Pierro T, Gaeta C, Carratù M, Neri P. Tetrahedron Lett. 2009; 50: 4416
• 9b Gaeta C, Troisi F, Talotta C, Pierro T, Neri P. J. Org. Chem. 2012; 77: 3634
• 10a Slavik P, Dudic M, Flidrova K, Sykora J, Cisarova I, Böhm S, Lhotak P. Org. Lett. 2012; 14: 3628
• 10b Flídrová K, Böhm S, Dvořáková H, Eigner V, Lhoták P. Org. Lett. 2014; 16: 138
• 10c Lhoták P. Org. Biomol. Chem. 2022; 20: 7377
• 11 Zhang Y.-Z, Xu M.-M, Si X-G, Hou J.-L, Cai Q. J. Am. Chem. Soc. 2022; 144: 22858
• 12 Zhang X, Tong S, Zhu J, Wang M.-X. Chem. Sci 2023; 14: 827

For recent reviews on inherently chiral calixarenes, see:
• 13a McIldowie MJ, Mocerino M, Ogden MI. Supramol. Chem. 2010; 22: 13
• 13b Li S.-Y, Xu Y.-W, Liu J.-M, Su C.-Y. Int. J. Mol. Sci. 2011; 12: 429
• 13c Zheng Y.-S, Luo J. J. Inclusion Phenom. Macrocyclic Chem. 2011; 71: 35
• 13d See ref. 8c
• 13e See ref. 10c
• 14a Xia Y.-X, Zhou H.-H, Shi J, Li S.-Z, Zhang M, Luo J, Xiang G.-Y. J. Inclusion Phenom. Macrocyclic Chem. 2012; 74: 277
• 14b Shi J, Li S.-Z, Xia Y.-X, Wang X.-G, Luo J, Wan Q. J. Inclusion Phenom. Macrocyclic Chem. 2013; 77: 327
• 14c Yang K, Li S.-Z, Wang Y.-H, Zhang W.-Z, Xu Z.-H, Zhou X.-Y, Zhu R.-X, Luo J, Wan Q. RSC Adv. 2014; 4: 6517
• 14d Luo J, Shen L.-C, Chung W.-S. J. Org. Chem. 2010; 75: 464
• 14e Li S.-Z, Shi J, Yang K, Luo J. Tetrahedron 2012; 68: 8557
• 14f Li S.-Z, Yang K, Liu H.-B, Xia Y.-X, Zhu R.-X, Luo J, Wan Q. Tetrahedron Lett. 2013; 54: 5901
• 14g Zhang W.-Z, Yang K, Li S.-Z, Ma H, Luo J, Wang K.-P, Chung W.-S. Eur. J. Org. Chem. 2015; 765
• 15a Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
• 15b Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
• 16a Jaime C, de Mendoza J, Prados P, Nieto PM, Sanchez C. J. Org. Chem. 1991; 56: 3372
• 16b Magrans JO, de Mendoza J, Pons M, Prados P. J. Org. Chem. 1997; 62: 4518
• 17 Maton L, Taziaux D, Soumillion J.-P, Habib Jiwan J.-L. J. Mater. Chem. 2005; 15: 2928
• 18 IUPAC 1968 Tentative Rules, Section E, Fundamental Stereochemistry, in: IUPAC-IUB Comm. on Biochem. Nomenclature; J. Org. Chem. 1970, 35, 2849.
• 19a Cielen E, Tahri A, Ver Heyen K, Hoornaert GJ, De Schryver FC, Boens N. J. Chem. Soc., Perkin Trans. 2 1998; 1573
• 19b de Silva AP, Gunaratne HQ. N. J. Chem. Soc., Chem. Commun. 1990; 186
• 20 Stern O, Volmer M. Phys. Z. 1919; 20: 183
• 21 Qing G.-Y, Qin H.-J, He Y.-B, Hu C.-G, Wang F, Hu L. Supramol. Chem. 2008; 20: 265

For our work using click chemistry to functionalize calix[4]arene as ion sensors, please see:
• 22a Chen Y.-J, Chen M.-Y, Lee K.-T, Shen L.-C, Hung H.-C, Niu H.-C, Chung W.-S. Front. Chem. 2020; 8: 593261
• 22b Su P.-M, Chang K.-C, Yang C.-J, Liu Y.-C, Chung W.-S. Chem. Commun. 2017; 53: 13241
• 22c Tsai C.-C, Cheng Y.-T, Shen L.-C, Chang K.-C, Ho I.-T, Chu J.-H, Chung W.-S. Org. Lett. 2013; 15: 5830
• 22d Tsai C.-C, Chang K.-C, Ho I.-T, Chu J.-H, Cheng Y.-T, Shen L.-C, Chung W.-S. Chem. Commun. 2013; 49: 3037
• 22e Wang N.-J, Sun J.-M, Chung W.-S. Sens. Actuators, B 2012; 171–172: 984
• 22f Ho I.-T, Haung K.-C, Chung W.-S. Chem. Asian J. 2011; 6: 2738
• 22g Wang N.-J, Sun J.-M, Chung W.-S. Tetrahedron 2011; 67: 8131
• 22h Chang K.-C, Su I.-H, Senthilvelan A, Chung W.-S. Org. Lett. 2007; 9: 3363