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Synthesis, structural analysis, and photophysical properties of bi-1,2,3-triazoles

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Abstract

Structural insights of a group of bi-1,2,3-triazoles derived from oxidative CuAAC are described through an X-ray crystallography study, distinguishing a dihedral angle which is ranged from 76.45 to 86.39° between the two 1,2,3-triazole rings. In addition, compound 1 containing a phenyl moiety displays a strong blue emission (λem = 394 nm); this structure-related photoluminescence is attributed to the rigidity of the molecule and the conjugation between phenyl groups and the triazole fragments.

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References

  1. Santana-Martinez I, Cuevas-Yañez E (2017) Bi-1,2,3-Triazoles: Synthesis and Perspectives. In: Chen Y, Tong ZR (eds) Click chemistry: approaches, applications and challenges. Nova Science Publishers, New York, pp 51–68

    Google Scholar 

  2. Zheng ZJ, Wang D, Xu Z, Xu LW (2015) Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: a family of valuable products by click chemistry. Beilstein J Org Chem 11:2557–25776

    Article  CAS  Google Scholar 

  3. Angell Y, Burgess K (2007) Base dependence in copper-catalyzed Huisgen reactions: efficient formation of bistriazoles. Angew Chem Int Ed 46:3649–3651

    Article  CAS  Google Scholar 

  4. Monkowius U, Ritter S, König B, Zabel M, Yersin H (2005) Synthesis, characterisation and ligand properties of novel bi-1,2,3-triazole ligands. Eur J Inorg Chem:4597–4606

    Article  Google Scholar 

  5. Brassard CJ, Zhang X, Brewer CR, Liu P, Clark RJ, Zhu L (2016) Cu (II)-catalyzed oxidative formation of 5,5′-bistriazoles. J Organomet Chem 81:12091–12105

    Article  CAS  Google Scholar 

  6. Key JA, Cairo CW, Ferguson MJ (2008) 7,70-(3,30-Dibenzyl-3H,30H-4,40-bi-1,2,3-triazole-5,500-diyl)bis(4-methyl-2hchromen-2-one). Acta Crystallogr E E64: o1910.

  7. Miyanishi S, Zhang Y, Hashimoto K, Tajima K (2012) Controlled synthesis of fullerene-attached poly(3-alkylthiophene)-based copolymers for rational morphological design in polymer photovoltaic devices. Macromolecules 45:6424–6437

    Article  CAS  Google Scholar 

  8. de la Cerda-Pedro JE, Rojas-Lima S, Santillan R, López-Ruiz H (2015) Phenylboronic Acid/CuSO4 as an efficient catalyst for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal acetylenes and alkyl azides. J Mex Chem Soc 59:130–136

    Google Scholar 

  9. Kwon M, Jang Y, Yoon S, Yang D, Jeon HB (2012) Unusual Cu(I)-catalyzed 1,3-dipolar cycloaddition of acetylenic amides: formation of bistriazoles. Tetrahedron Lett 53:1606–1609

    Article  CAS  Google Scholar 

  10. Goyard D, Chajistamatiou AS, Sotiropoulou AI, Chrysina ED, Praly JP, Vidal S (2014) Efficient atropodiastereoselective access to 5,5’-bis-1,2,3-triazoles: studies on 1-glucosylated 5-halogeno 1,2,3-triazoles and their 5-substituted derivatives as glycogen phosphorylase inhibitors. Chem Eur J 20:5423–5432

    Article  CAS  Google Scholar 

  11. González J, Pérez VM, Jiménez DO, Lopez-Valdez G, Corona D, Cuevas-Yañez E (2011) Effect of temperature on triazole and bistriazole formation through copper-catalyzed alkyne–azide cycloaddition. Tetrahedron Lett 52:3514–3517

    Article  Google Scholar 

  12. Parmar D, Sugiono E, Raja S, Rueping M (2014) Complete field guide to asymmetric binol-phosphate derived Brønsted acid and metal catalysis: history and classification by mode of activation; Brønsted acidity, hydrogen bonding, ion pairing, and metal phosphates. Chem Rev 114:9047–9153

    Article  CAS  Google Scholar 

  13. Brunel JM (2005) BINOL: a versatile chiral reagent. Chem Rev 105:857–898

    Article  CAS  Google Scholar 

  14. Chen Y, Yekta S, Yudin AK (2003) Modified BINOL ligands in asymmetric catalysis. Chem Rev 103:3155–3212

    Article  CAS  Google Scholar 

  15. Kaes C, Katz A, Hosseini MW (2000) Bipyridine: the most widely used ligand. A review of molecules comprising at least two 2,2’-bipyridine units. Chem Rev 100:3553–3590

    Article  CAS  Google Scholar 

  16. Murata T, Yakiyama Y, Nakasuji K, Morita Y (2010) Supramolecular architectures and hydrogen-bond directionalities of 4,40-biimidazole metal complexes depending on coordination geometries. Cryst Growth Des 10:4898–4905

    Article  CAS  Google Scholar 

  17. Kennedy DC, James BR (2010) Syntheses of ruthenium(II)-4,4’-biimidazole complexes and their potential anti-tumour activity. Can J Chem 88:886–892

    Article  CAS  Google Scholar 

  18. Baig RBN, Varma RS (2013) Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites. Green Chem 15:398–417

    Article  Google Scholar 

  19. Luque R, Baruwati B, Varma RS (2010) Magnetically separable nanoferrite-anchored glutathione: aqueous homocoupling of arylboronic acids under microwave irradiation. Green Chem 12:1540–1543

    Article  CAS  Google Scholar 

  20. Liu X, Gao W, Sun P, Su Z, Chen S, Wei Q, Xie G, Gao S (2015) Environmentally friendly high-energy MOFs: crystal structures, thermostability, insensitivity and remarkable detonation performances. Green Chem 17:831–836

    Article  CAS  Google Scholar 

  21. Wang XL, Cao JJ, Liu GC, Tian AX, Luan J, Lin HY, Zhang JW, Li N (2014) Keggin-based 3D frameworks tuned by silver polymeric motifs: effect of the bi(triazole) substituent group on the architectures. CrystEngComm 16:5732–5740

    Article  CAS  Google Scholar 

  22. Katan C, Savel P, Wong BM, Roisnel T, Dorcet V, Fillaut JL, Jacquemin D (2014) Absorption and fluorescence signatures of 1,2,3-triazole based regioisomers: challenging compounds for TD-DFT. Phys Chem Chem Phys 16:9064–9073

    Article  CAS  Google Scholar 

  23. Ghosh D, Rhodes S, Hawkins K, Winder D, Atkinson A, Ming W, Padgett C, Orvis J, Aiken K, Landge S (2015) A simple and effective 1,2,3-triazole based “turn-on” fluorescence sensor for the detection of anions. New J Chem 39:295–303

    Article  CAS  Google Scholar 

  24. White NG, Beer PD (2013) A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition. Org Biomol Chem 11:1326–1333

    Article  CAS  Google Scholar 

  25. Lee IL, Sung YM, Wu CH (2014) Wu SP (2014) Colorimetric sensing of iodide based on triazole-acetamide functionalized gold nanoparticles. Microchim Acta 181:573–579

    Article  CAS  Google Scholar 

  26. Fernández-Hernández JM, Beltrán JI, Lemaur V, Gálvez-López MD, Chien CH, Polo F, Orselli E, Fröhlich R, Cornil J, De Cola L (2013) Iridium(III) emitters based on 1,4-disubstituted-1H-1,2,3-triazoles as cyclometalating ligand: synthesis, characterization, and electroluminescent deviceS. Inorg Chem 52:1812–1824

    Article  Google Scholar 

  27. Hao E, Meng ZTM, Pang W, Zhou Y, Jiao L (2011) Solvent dependent fluorescent properties of a 1,2,3-triazole linked 8-hydroxyquinoline chemosensor: tunable detection from zinc(II) to Iron(III) in the CH3CN/H2O System. J Phys Chem A 115:8234–8241

    Article  CAS  Google Scholar 

  28. Kim SH, Choi HS, Kim J, Lee SJ, Quango DT, Kim JS (2010) Novel optical/electrochemical selective 1,2,3-triazole ring-appended chemosensor for the Al3+ ion. Org Lett 12:560–563

    Article  CAS  Google Scholar 

  29. Erdemir S, Kocyigit O, Malkondu SJ (2015) Detection of Hg2+ ion in aqueous media by new fluorometric and colorimetric sensor based on triazole–rhodamine. J Photochem Photobiol A 309:15–21

    Article  CAS  Google Scholar 

  30. AEl-Betany AMM, McKeown NB (2012) The synthesis and fluorescence properties of macromolecular components based on 1,8-naphthalimide derivatives and dimers. Tetrahedron Lett 53:808–810

    Article  Google Scholar 

  31. Zoon PD, Van Stokkum IHM, IHM PM, Mongin O, Blanchard-Desce M, Brouwer AM (2010) Fast photo-processes in triazole-based push–pull systems. Phys Chem Chem Phys 12:2706–2715

    Article  CAS  Google Scholar 

  32. Zhou Z, Fahrni CJ (2004) A fluorogenic probe for the copper(I)-catalyzed azide−alkyne ligation reaction: modulation of the fluorescence emission via 3(n,π*)−(π,π*) inversion. J Am Chem Soc 126:8862–8863

    Article  CAS  Google Scholar 

  33. Parent M, Mongin O, Kamada K, Katan C, Blanchard-Desce M (2005) New chromophores from click chemistry for two-photon absorption and tuneable photoluminescence. Chem Commun:2029–2031

  34. Welby CE, Grkinic S, Zahid A, Uppal BS, Gibson EA, Rice CR, Elliott PIP (2012) Synthesis, characterisation and theoretical study of ruthenium 4,4′-bi-1,2,3-triazolyl complexes: fundamental switching of the nature of S1 and T1 states from MLCT to MC. Dalton Trans 41:7637–7646

    Article  CAS  Google Scholar 

  35. Welby CE, Armitage GK, Bartley H, Sinopoli A, Uppal BS, Elliott PIP (2014) Photochemical ligand ejection from non-sterically promoted Ru(II)bis(diimine) 4,4’-bi-1,2,3-triazolyl complexes. Photochem Photobiol Sci 13:735–738

    Article  CAS  Google Scholar 

  36. Welby CE, Gilmartin L, Marriott RR, Zahid A, Rice CR, Gibson EA, Elliott PIP (2013) Luminescent biscyclometalated arylpyridine iridium(III) complexes with 4,4’-bi-1,2,3-triazolyl ancillary ligands. Dalton Trans 42:13527–13536

    Article  CAS  Google Scholar 

  37. Ross DAW, Scattergood PA, Babaei A, Pertegás A, Bolink HJ, Elliott PIP (2016) Luminescent osmium(II) bi-1,2,3-triazol-4-yl complexes: photophysical characterisation and application in light-emitting electrochemical cells. Dalton Trans 45:7748–7757

    Article  CAS  Google Scholar 

  38. García MA, Ríos ZG, González J, Pérez VM, Lara N, Fuentes A, González C, Corona D, Cuevas-Yañez E (2011) The use of glucose as alternative reducing agent in copper-catalyzed alkyne-azide cycloaddition. Lett Org Chem 8:701–706

    Article  Google Scholar 

  39. Scattergood PA, Sinopoli A, Elliott PIP (2017) Photophysics and photochemistry of 1,2,3-triazole-based complexes. Coord Chem Rev 350:136–154

    Article  CAS  Google Scholar 

  40. Rendón-Balboa JC, Villanueva-Sánchez L, Rosales-Vázquez LD, Valdes-García J, Vilchis-Nestor AR, Martínez-Otero D, Martínez-Vargas S, Dorazco-González A (2018) Structure of a luminescent 3D coordination polymer constructed with a trinuclear core of cadmium-trimesate and isoquinoline. Inorg Chim Acta 483:235–240

    Article  Google Scholar 

  41. Jarowski PD, Wu YL, Schweizer WB, Diederich F (2008) 1,2,3-Triazoles as conjugative π-linkers in push−pull chromophores: importance of substituent positioning on intramolecular charge-transfer. Org Lett 10:3347–3350

    Article  CAS  Google Scholar 

  42. Yan W, Wang Q, Lin Q, Li M, Petersen JL, Shi X (2011) N-2-Aryl-1,2,3-triazoles: A novel class of UV/blue-light-emitting fluorophores with tunable optical properties. Chem Eur J 17:5011–5018

    Article  CAS  Google Scholar 

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Acknowledgments

The authors would like to thank N. Zavala, A. Nuñez, and L. Triana for the technical support.

Funding

Financial support from CONACYT is gratefully acknowledged.

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Authors and Affiliations

  1. Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Universidad Autónoma del Estado de México, Carretera Toluca-Atlacomulco Km 14.5, 50200, Toluca, State of Mexico, Mexico

    Ivette Santana-Martínez, María Teresa Ramírez-Palma, Javier Sánchez-Escalera, Diego Martínez-Otero, Marco A. García-Eleno, Alejandro Dorazco-González & Erick Cuevas-Yañez

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  1. Ivette Santana-Martínez
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  2. María Teresa Ramírez-Palma
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Correspondence to Erick Cuevas-Yañez.

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Santana-Martínez, I., Ramírez-Palma, M.T., Sánchez-Escalera, J. et al. Synthesis, structural analysis, and photophysical properties of bi-1,2,3-triazoles. Struct Chem 31, 191–201 (2020). https://doi.org/10.1007/s11224-019-01390-1

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