Synthesis 2023; 55(17): 2786-2796
paper
Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry
Synthesis and Optical Resolution of Inherently Chiral Fluorescent Calix[4]arenes and Their Application in Chiral Recognition
Fu-Ming Yang
a
Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan 30050
,
Jun Luo∗
a
Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan 30050
b
Tongji School of Pharmacy, Huazhong University of Science and Technology, Wuhan 430030, P. R. of China
,
Yi-Chieh Chen
c
Department of Applied Chemistry, National Yang Ming Chiao Tung University, Hsinchu, Taiwan 30050
,
a
Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan 30050
c
Department of Applied Chemistry, National Yang Ming Chiao Tung University, Hsinchu, Taiwan 30050
› Institutsangaben We thank the Ministry of Science and Technology, Taiwan for funding support (grant numbers MOST-108-2113-M-009-006, MOST-109-2113-M-009-016, MOST-110-2113-M-A49-009, and MOST-111-2113-M-A49-023).
This paper is dedicated to Prof. Guoqiang Lin on the occasion of his 80th 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
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751455.
Supporting Information
Publikationsverlauf
Eingereicht: 24. März 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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
