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DOI: 10.1055/a-2637-5758
One-pot Synthesis and Photoswitching Properties of Bis-triazole-linked Macrocyclic Glycoazobenzene
Supported by: Direction Générale de l’Armement Master internship
Supported by: China Scholarship Council (CSC)
Abstract
Photoswitchable glycomacrocycles are of great interest because of their intrinsic chirality, their variable ring sizes, molecular shapes, and their potential applications in chemistry, materials science, biology, and drug discovery. Through a one-pot double click reaction, we have successfully synthesized a new 20-membered azobenzene-based glycomacrocycle bearing two triazole rings. The macrocyclization conditions have been optimized to achieve a yield of up to 55% for the synthesis of hundreds of milligrams of the compound E-1. The macrocyclic glycoazobenzene E-1 can be reversibly photoisomerized between E and Z isomers, with good photoconversion yields, high fatigue resistance, and bistability of both E and Z isomers. The X-ray structures have been obtained for both E- and Z-isomers of 1. The chiroptical activity has also been observed with the E-1.
Publication History
Received: 03 April 2025
Accepted after revision: 16 June 2025
Article published online:
24 July 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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References
- 1 Renner C, Moroder L. Chem Bio Chem 2006; 7: 868-878
- 2 Reuter R, Wegner HA. Chem Commun 2011; 47: 12267-12276
- 3 Wagner-Wysiecka E, Łukasik N, Biernat JF, Luboch E. J Incl Phenom Macrocycl Chem 2018; 90: 189-257
- 4 Vlasceanu A, Cacciarini M, Nielsen MB. Tetrahedron 2018; 74: 6635-6646
- 5 Yu J, Qi D, Li J. Commun Chem 2020; 3: 189
- 6 Xie J. In Carbohydrate Chemistry: Chemical and Biological Approaches. Rauter AP, Lindhorst TK, Queneau Y. edsVol 45. Cambridge: Royal Society of Chemistry; 2021: 460-498
- 7 Yang Z, Liu Z, Yuan L, Asian J. Org Chem 2021; 10: 74-90
- 8 Ludwig C, Xie J. Chem Photo Chem 2023; 7: e202300126
- 9 Afonin S, Babii O, Reuter A. et al. Beilstein J Org Chem 2020; 16: 39-49
- 10 Cataldi E, Raschig M, Gutmann M. et al. Chem Bio Chem 2023; 24: e202200570
- 11 Kalyvas JT, Facal Marina P, Stachura DL, Horsley JR, Abell AD. Chem Eur J 2023; 29: e202301487
- 12 Villarόn D, Brugman GEA, Sieglerb MA, Wezenberg SJ. Chem Commun 2023; 59: 8688-8691
- 13 Sahoo D, Majeed AA, Lathwal A, De S. Chem Eur J 2023; 29: e202300092
- 14 Xiong S, Zhang Y, Jiang Y. et al. Chem Commun 2023; 59: 12994-12997
- 15 Liu Y, Wang H, Liu P. et al. Angew Chem Int Ed 2021; 60: 5766-5770
- 16 Falkenburg R, Notheis MJ, Schnakenburg G, von Krbek LKS. Org Biomol Chem 2023; 21: 4993-4998
- 17 Ghosh S, Eschen C, Eleya N, Staubitz A. J Org Chem 2023; 88: 3372-3377
- 18 Zhang F, Rao Y, Zhou M, Xu L, Osuka A, Song J. Chem Eur J 2023; 29: e202302340
- 19 Wang H, Tang Y, Li Q. Angew Chem Int Ed 2023; 62: e202216600
- 20 De Jong J, Siegler MA, Wezenberg SJ. Angew Chem Int Ed 2024; 63: e202316628
- 21 Despras G, Hain J, Jaeschke S. Chem Eur J 2017; 23: 10838-10847
- 22 Hain J, Despras G. Chem Commun 2018; 54: 8563-8566
- 23 Lin C, Maisonneuve S, Métivier R, Xie J. Chem Eur J 2017; 23: 14996-15001
- 24 Lin C, Maisonneuve S, Theulier C, Xie J. Eur J Org Chem 2019; 1770-1777
- 25 Kim Y, Mafy N, Maisonneuve S, Lin C, Tamaoki N, Xie J. ACS Appl Mater Interfaces 2020; 12: 52146-52155
- 26 Lin C, Jiao J, Maisonneuve S, Mallétroit J, Xie J. Chem Commun 2020; 56: 3261-3264
- 27 Jiao J, Maisonneuve S, Xie J. J Org Chem 2022; 87: 8534-8543
- 28 Jiao J, Xie J. Synthesis 2024; 86: 2681-2686
- 29 Sokolowska P, Dabrowa K, Jarosz S. Org Lett 2021; 23: 2687-2692
- 30 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew Chem Int Ed 2002; 41: 2596-2599
- 31 Tornoe CW, Christensen C, Meldal M. J Org Chem 2002; 67: 3057-3069
- 32 Miller JN, Pongdee R. Tetrahedron Lett 2013; 54: 3185-3187
- 33 Song C-X, Szulwach KE, Fu Y. et al. Nat Biotechnol 2011; 29: 68-72
- 34 McDonnell C, Cronin L, O’Brien JL, Murphy PV. J Org Chem 2004; 69: 3565-3568
- 35 Maschauer S, Haubner R, Kuwert T, Prante O. Mol Phramaceutics 2014; 11: 505-515
- 36 Haridas V, Lal K, Sharma YK, Upreti S. Org Lett 2008; 10: 1645-1647
- 37 Lau YH, de Andrade P, Quah S-T. et al. Chem Sci 2014; 5: 1804-1809
- 38 Kappe CO, Van der Eycken E. Chem Soc Rev 2010; 39: 1280-1290
- 39 Hein JE, Fokin VV. Chem Soc Rev 2010; 39: 1302-1315