Synthesis, Spectroscopic, and Photophysical Studies of Phosphorescent Bis(2-(2,4-difluorophenyl)pyridine)Iridium(III) Complex Containing Derivative of 1H-1,2,4-Triazole Anchillary Ligand

https://doi.org/10.22146/ijc.66471

Nurul Husna As Saedah Bain(1), Noorshida Mohd Ali(2*), Yusnita Juahir(3), Norhayati Hashim(4), Illyas Md Isa(5), Azmi Mohamed(6), Azlan Kamari(7), Bohari Mohd Yamin(8)

(1) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
(2) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
(3) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
(4) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
(5) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
(6) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
(7) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
(8) Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bandar Baru Bangi, Selangor, Malaysia
(*) Corresponding Author

Abstract


A cationic complex of iridium(III), [Ir(2,4-F2ppy)2(F2bpyta)]PF6 utilizing 1,2,4-triazolepyridyl as an anchillary ligand modified with a 2,6-difluorobenzyl substituent was synthesized and characterized. The aromatic signals of pyridyltriazole and phenylpyridine proton were detected in the 1H-NMR spectrum between 10.00 and 7.00 ppm. Only one singlet peak was detected at 8.46 ppm H(8) shifted to the upfield, demonstrating that C5 was coordinated to the central iridium metal. The bands exhibited in the range of 1555–1431 cm–1 in the IR spectrum because of the C=C and C=N aromatic rings stretching pyridine, phenyl, and triazole vibrations. The UV-Vis absorption spectrum showed a slight and broad absorbance peak at lower energy at a lmax = 371 nm (e = 6129 M−1 cm−1) in the visible range due to 1MLCT and 3MLCT transitions. Blue emission was observed in the steady-state emission spectral of [Ir(2,4-F2ppy)2(F2bpyta)]PF6 and the other two previously synthesized iridium(III) complexes in CH2Cl2 solutions (air-equilibrated) at room temperature. The spectrum of luminescence for the [Ir(2,4-F2ppy)2(F2bpyta)]PF6 (lem = 461 nm) is blue-shifted when compared to the [Ir(2,4-F2ppy)2(hpyta)]PF6 (lem = 469 nm), but red-shifted when related to the [Ir(2,4-F2ppy)2(mbpyta)]PF6 (lem = 454 nm).


Keywords


iridium(III) complex; 1H-1,2,4-triazole; ancillary ligand



References

[1] Ali, N.M., Ward, M.D., Hashim, N., and Daud, N., 2017, Synthesis and photophysical properties of bis(phenylpyridine) iridium(III) dicyanide complexes, Mater. Res. Innovations, 23 (3), 135–140.

[2] Barbante, G.J., Doeven, E.H., Francis, P.S., Stringer, B.D., Hogan, C.F., Kheradmand, P.R., Wilson, D.J.D., and Barnard, P.J., 2015, Iridium(III) N-heterocyclic carbene complexes: An experimental and theoretical study of structural, spectroscopic, electrochemical and electrogenerated chemiluminescence properties, Dalton Trans., 44 (18), 8564–8576.

[3] Lee, S., and Han, W.S., 2020, Cyclometalated Ir(III) complexes towards blue-emissive dopant for organic light-emitting diodes: fundamentals of photophysics and designing strategies, Inorg. Chem. Front., 7 (12), 2396–2422.

[4] Si, Y., Zang, S., Gahungu, G., Yang, J., and Wu, Z., 2015, Modification of the emission colour and quantum efficiency for oxazoline- and thiazoline- containing Iridium complexes via different N^O, RSC Adv., 5 (24), 18464–18470

[5] Costa, R.D., Ortí, E., Bolink, H.J., Monti, F., Accorsi, G., and Armaroli, N., 2012, Luminescent ionic transition-metal complexes for light-emitting electrochemical cells, Angew. Chem. Int. Ed., 51 (33), 8178–8211.

[6] Adeloye, A.O., Mphahlele, M.J., Adekunle, A.S., Rhyman, L., and Ramasami, P., 2017, Spectroscopic, electrochemical and DFT studies of phosphorescent homoleptic cyclometalated iridium(III) complexes based on substituted 4-fluorophenylvinyland 4-methoxyphenylvinylquinolines, Materials, 10 (10), 1061.

[7] Aghazada, S., Huckaba, A.J., Ojeda, A.P., Babaei, A., Grancini, G., Zimmermann, I., Bolink, H., and Nazeeruddin, M.K., 2016, Molecular engineering of iridium blue emitters using aryl N-heterocyclic carbene ligands, Eur. J. Inorg. Chem., 2016 (32), 5089–5097.

[8] Li, H., Yin, Y.M., Cao, H.T., Sun, H.Z., Wang, L., Shan, G.G., Zhu, D.X., Su, Z.M., and Xie, W.F., 2014, Efficient greenish-blue phosphorescent iridium(III) complexes containing carbene and triazole chromophores for organic light-emitting diodes, J. Organomet. Chem., 753, 55–62.

[9] Flifel, I.A., and Hlail, A.N., 2017, Preparation, spectra characterization of new 1,2,4-triazole derivatives and its complexities with some transition metal ions, Int. J. Appl. Eng. Res., 12 (24), 14878–14881.

[10] Pal, A.K., Cordes, D.B., Pringouri, K., Anwar, M.U., Slawin, A.M.Z., Rawson, J.M., and Zysman-Colman, E., 2016, Synthesis and characterization of green-to-yellow emissive Ir(III) complexes of pyridylbenzothiadiazine ligand, J. Coord. Chem., 69 (11-13), 1924–1937.

[11] Rentzsch, C.F., Tosh, E., Herrmann, W.A., and Kühn, F.E., 2009, Iridium complexes of N-heterocyclic carbenes in C–H borylation using energy efficient microwave technology: Influence of structure, ligand donor strength and counter ion on catalytic activity, Green Chem., 11 (10), 1610–1617.

[12] Omae, I., 2016, Application of the five-membered ring blue light-emitting iridium products of cyclometalation reactions as OLEDs, Coord. Chem. Rev., 310, 154–169.

[13] Ahn, S.Y., Lee, H.S., and Ha, Y., 2011, New blue phosphorescent iridium complexes containing phenylpyridine and triazole ligands: Synthesis and luminescence studies, J. Nanosci. Nanotechnol., 11 (5), 4414–4418.

[14] Bain, N.H.A.S., Ali, N.M., Juahir, Y., Hashim, N., Isa, I.M., Mohamed, A., Kamari, A., Anouar, E.H., Yamin, B.M., Tajuddin, A.M., and Baharudin, M.H., 2020, Synthesis, crystal structure, photophysical properties, DFT studies and Hirshfeld surface analysis of a phosphorescent 1,2,4-triazole-based iridium(III) complex, Polyhedron, 188, 114690.

[15] Bain, N.H.A.S., Ali, N.M., Juahir, Y., Hashim, N., Isa, I.M., Mohamed, A., Kamari, A., and Yamin, B.M., 2018, Synthesis of phenylpyridine iridium(III) complexes with N-heterocyclic carbene as ancillary ligands, IOP Conf. Ser.: Mater. Sci. Eng., 440, 012010.

[16] Henwood, A.F., Bansal, A.K., Cordes, D.B., Slawin, A.M.Z., Samuel, I.D.W., and Zysman-Colman, E., 2016, Solubilised bright blue-emitting iridium complexes for solution processed OLEDs, J. Mater. Chem. C, 4 (17), 3726–3737.

[17] Barbante, G.J., Francis, P.S., Hogan, C.F., Kheradmand, P.R., Wilson, D.J.D., and Barnard, P.J., 2013, Electrochemiluminescent ruthenium(II) N-heterocyclic carbene complexes: A combined experimental and theoretical study, Inorg. Chem., 52 (13), 7448–7459.

[18] He, L., Wang, Z., Duan, L., Yang, C., Tang, R., Song, X., and Pan, C., 2016, Toward fluorine-free blue-emitting cationic iridium complexes: To generate emission from the cyclometalating ligands with enhanced triplet energy, Dalton Trans., 45 (13), 5604–5613.

[19] Gökce, H., Öztürk, N., Taşan, M., Alpaslan, Y.B., and Alpaslan, G., 2016, Spectroscopic characterization and quantum chemical computations of the 5-(4-pyridyl)-1H-1,2,4-triazole-3-thiol molecule, Spectrosc. Lett., 49 (3), 167–179.

[20] Beldovskaya, A.D., Dushenko, G.A., and Vikrishchuk, N.I., 2013, Synthesis, structure, and spectral luminescent properties of novel 1,2,4-triazole derivatives containing benzthiazole group, Russ. J. Gen. Chem., 83 (11), 2075–2083.

[21] Sanner, R.D., Cherepy, N.J., and Young, V.G., 2016, Blue light emission from cyclometallated iridium(III) cyano complexes: Syntheses, crystal structures, and photophysical properties, Inorg. Chim. Acta, 440, 165–171.

[22] Stringer, B.D., Quan, L.M., Barnard, P.J., Wilson, D.J.D., and Hogan, C.F., 2014, Iridium complexes of N-heterocyclic carbene ligands: Investigation into the energetic requirements for efficient electrogenerated chemiluminescence, Organometallics, 33 (18), 4860–4872.

[23] Monti, F., Kessler, F., Delgado, M., Frey, J., Bazzanini, F., Accorsi, G., Armaroli, N., Bolink, H.J., Orti, E., Scopelliti, R., Nazeeruddin, M.K., and Baranoff, E., 2013, Charged bis-cyclometalated iridium(III) complexes with carbene-based ancillary ligands, Inorg. Chem., 52 (18), 10292–10305.

[24] Baranoff, E., Curchod, B.F.E., Monti, F., Steimer, F., Accorsi, G., Tavernelli, I., Rothlisberger, U., Scopelliti, R., Grätzel, M., and Nazeeruddin, M.K., 2012, Influence of halogen atoms on a homologous series of bis-cyclometalated iridium(III) complexes, Inorg. Chem., 51 (2), 799–811.

[25] Pla, P., Junquera-Hernández, J.M., Bolink, H.J., and Ortí, E., 2015, Emission energy of azole-based ionic iridium(III) complexes: A theoretical study, Dalton Trans., 44 (18), 8497–8505.

[26] Tamayo, A.B., Alleyne, B.D., Djurovich, P.I., Lamansky, S., Tsyba, I., Ho, N.N., Bau, R., and Thompson, M.E., 2013, Synthesis and characterization of facial and meridional tris-cyclometalated iridium(III) complexes, J. Am. Chem. Soc., 125 (24), 7377–7387.

[27] Wang, Z., He, L., Duan, L., Yan, J., Tang, R., Pan, C., and Song, X., 2015, Blue-green emitting cationic iridium complexes with 1,3,4-oxadiazole cyclometallating ligands: Synthesis, photophysical and electrochemical properties, theoretical investigation and electroluminescent devices, Dalton Trans., 44 (36), 15914–15923.



DOI: https://doi.org/10.22146/ijc.66471

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