Phosphorescent Platinum(II) Complexes with a Spiro-fused Xanthene Unit: Synthesis and Photophysical Properties.

NHC Phosphorescence Platinum(II) Regioisomerism Spirocycles

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)

ISSN: 1521-3765

Titre abrégé: Chemistry

Pays: Germany

ID NLM: 9513783

Informations de publication

Date de publication:
07 Mar 2024

Historique:

received: 20 12 2023

medline: 7 3 2024

pubmed: 7 3 2024

entrez: 7 3 2024

Statut: aheadofprint

Résumé

Novel platinum(II) complexes, derived from the spiro[fluorene-9,9'-xanthene] (SFX) motif, were synthesized and combined with different auxiliary ligands such as acetylacetonate (acac), bis(2,4,6-trimethylphenyl)propane-1,3-dionate (mesacac) and dihydrobis(3,5-dimethylpyrazole-1-yl) borate. The final products were obtained in yields of up to 36 % and characterized by NMR, X-ray and combustion analysis. These complexes have structured green-blue emission spectra with Commission Internationale de l'Éclairage (CIE

Identifiants

DOI: 10.1002/chem.202304263 PMID: 38450788

pubmed: 38450788

doi: 10.1002/chem.202304263

doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

Pagination

e202304263

Informations de copyright

Références

G. Hong, X. Gan, C. Leonhardt, Z. Zhang, J. Seibert, J. M. Busch, S. Bräse, Adv. Mater. 2021, 33, e2005630.

C. W. Tang, S. A. van Slyke, Appl. Phys. Lett. 1987, 51, 913-915.

Y. Chen, J. Jayakumar, C. Hsieh, T. Wu, C. Liao, J. Pandidurai, C. Ko, W. Hung, C. Cheng, Adv. Mater. 2021, 33, e2008032.

T. Fleetham, G. Li, J. Li, Adv. Mater. 2017, 29, 1601861.

Y. Fu, H. Liu, D. Yang, D. Ma, Z. Zhao, B. Z. Tang, Sci. Adv. 2021, 7, eabj2504.

H. Park, S. Ameen, R. Kumaresan, J. Lee, J. Park, D. Song, J. Lee, Y. Heo, B. Kim, S. Jin, Adv. Opt. Mater. 2023, 11, 2202641.

H. Shi, W. Jing, W. Liu, Y. Li, Z. Li, B. Qiao, S. Zhao, Z. Xu, D. Song, ACS Omega 2022, 7, 7893-7900.

H. Lee, R. Braveenth, S. Muruganantham, C. Y. Jeon, H. S. Lee, J. H. Kwon, Nat. Commun. 2023, 14, 419.

Q.-Y. Meng, R. Wang, Y.-L. Wang, X.-W. Guo, Y.-Q. Liu, X.-L. Wen, C.-Y. Yao, J. Qiao, Nat. Commun. 2023, 14, 3927.

J. Jin, Z. Zhu, J. Yan, X. Zhou, C. Cao, P.-T. Chou, Y.-X. Zhang, Z. Zheng, C.-S. Lee, Y. Chi, Adv. Photonics Res. 2022, 3, 2100381.

J. M. Ha, S. H. Hur, A. Pathak, J.-E. Jeong, H. Y. Woo, NPG Asia Mater. 2021, 13, 53.

M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151-154.

M. A. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R. Forrest, Appl. Phys. Lett. 1999, 75, 4-6.

S. Lee, W.-S. Han, Inorg. Chem. Front. 2020, 7, 2396-2422.

A. K. Pal, G. S. Hanan, Chem. Soc. Rev. 2014, 43, 6184-6197.

Y. Chi, B. Tong, P.-T. Chou, Coord. Chem. Rev. 2014, 281, 1-25.

T. Strassner, Acc. Chem. Res. 2016, 49, 2680-2689.

H. Yersin, in Highly Efficient OLEDs with Phosphorescent Materials, Wiley-VCH, Weinheim, 2007, pp. 1-89.

V. W.-W. Yam, A. K.-W. Chan, E. Y.-H. Hong, Nat. Rev. Chem. 2020, 4, 528-541.

L. P. Ravaro, K. P. S. Zanoni, A. S. S. Camargo, Energy Rep. 2020, 6, 37-45.

L. De Cola, P. Belser, A. Zelewsky, F. Vögtle, Inorg. Chim. Acta 2007, 360, 775-784.

S.-H. Chang, C.-F. Chang, J.-L. Liao, Y. Chi, D.-Y. Zhou, L.-S. Liao, T.-Y. Jiang, T.-P. Chou, E. Y. Li, G.-H. Lee, T.-Y. Kuo, P.-T. Chou, Inorg. Chem. 2013, 52, 5867-5875.

P. Chou, Y. Chi, Eur. J. Inorg. Chem. 2006, 2006, 3319-3332.

C. Adachi, M. A. Baldo, S. R. Forrest, M. E. Thompson, Appl. Phys. Lett. 2000, 77, 904-906.

C. Adachi, M. A. Baldo, M. E. Thompson, S. R. Forrest, Int. J. Appl. Phys. 2001, 90, 5048-5051.

S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H. E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304-4312.

X. Yang, X. Zhou, Y.-X. Zhang, D. Li, C. Li, C. You, T.-C. Chou, S.-J. Su, P.-T. Chou, Y. Chi, Adv. Sci. 2022, 9, e2201150.

J. Yan, D.-Y. Zhou, L.-S. Liao, M. Kuhn, X. Zhou, S.-M. Yiu, Y. Chi, Nat. Commun. 2023, 14, 6419.

H. Fu, Y.-M. Cheng, P.-T. Chou, Y. Chi, Mater. Today 2011, 14, 472-479.

A. Bonfiglio, M. Mauro, Eur. J. Inorg. Chem. 2020, 2020, 3427-3442.

C. F. R. Mackenzie, L. Zhang, D. B. Cordes, A. M. Z. Slawin, I. D. W. Samuel, E. Zysman-Colman, Adv. Opt. Mater. 2023, 11, 2201495.

P.-N. Lai, C. H. Brysacz, M. K. Alam, N. A. Ayoub, T. G. Gray, J. Bao, T. S. Teets, J. Am. Chem. Soc. 2018, 140, 10198-10207.

C. Cebrián, M. Mauro, Beilstein J. Org. Chem. 2018, 14, 1459-1481.

J. Kalinowski, V. Fattori, M. Cocchi, J. Gareth, A. Williams, Coord. Chem. Rev. 2011, 255, 2401-2425.

W. Paw, S. D. Cummings, M. Adnan Mansour, W. B. Connick, D. K. Geiger, R. Eisenberg, Coord. Chem. Rev. 1998, 171, 125-150.

K. Li, G. S. Ming Tong, Q. Wan, G. Cheng, W.-Y. Tong, W.-H. Ang, W.-L. Kwong, C.-M. Che, Chem. Sci. 2016, 7, 1653-1673.

C. A. Strassert, C.-H. Chien, M. D. Galvez Lopez, D. Kourkoulos, D. Hertel, K. Meerholz, L. Cola, Angew. Chem. Int. Ed. 2011, 50, 946-950.

C. Cebrián, M. Mauro, D. Kourkoulos, P. Mercandelli, D. Hertel, K. Meerholz, C. A. Strassert, L. Cola, Adv. Mater. 2013, 25, 437-442.

A. Galstyan, A. R. Naziruddin, C. Cebrián, A. Iordache, C. G. Daniliuc, L. Cola, C. A. Strassert, Eur. J. Inorg. Chem. 2015, 2015, 5822-5831.

C. F. Harris, D. A. K. Vezzu, L. Bartolotti, P. D. Boyle, S. Huo, Inorg. Chem. 2013, 52, 11711-11722.

T. Fleetham, Z. Wang, J. Li, Org. Electron. 2012, 13, 1430-1435.

X. Yang, Z. Wang, S. Madakuni, J. Li, G. E. Jabbour, Adv. Mater. 2008, 20, 2405-2409.

X. Zhang, A. M. Wright, N. J. DeYonker, T. K. Hollis, N. I. Hammer, C. E. Webster, E. J. Valente, Organometallics 2012, 31, 1664-1672.

J. Liu, T.-L. Lam, M.-K. Sit, Q. Wan, C. Yang, G. Cheng, C.-M. Che, J. Mater. Chem. C 2022, 10, 10271-10283.

Y. K. Moon, J.-S. Huh, S. Kim, S. Kim, S. Y. Yi, J.-J. Kim, Y. You, ACS Appl. Electron. Mater. 2020, 2, 604-617.

K. Li, G. Cheng, C. Ma, X. Guan, W.-M. Kwok, Y. Chen, W. Lu, C.-M. Che, Chem. Sci. 2013, 4, 2630.

D. A. K. Vezzu, J. C. Deaton, J. S. Jones, L. Bartolotti, C. F. Harris, A. P. Marchetti, M. Kondakova, R. D. Pike, S. Huo, Inorg. Chem. 2010, 49, 5107-5119.

K.-W. Lo, G. S. M. Tong, G. Cheng, K.-H. Low, C.-M. Che, Angew. Chem. Int. Ed. 2022, 61, e202115515.

J. Sun, H. Ahn, S. Kang, S.-B. Ko, D. Song, H. A. Um, S. Kim, Y. Lee, P. Jeon, S.-H. Hwang, Y. You, C. Chu, S. Kim, Nat. Photonics 2022, 16, 212-218.

H. Amouri, Chem. Rev. 2023, 123, 230-270.

M. Hruzd, S. Kahlal, N. Le Poul, L. Wojcik, M. Cordier, J.-Y. Saillard, J. Rodríguez-López, F. Robin-le Guen, S. Gauthier, S. Achelle, Dalton Trans. 2023, 52, 1927-1938.

J. Soellner, P. Pinter, S. Stipurin, T. Strassner, Angew. Chem. Int. Ed. 2021, 60, 3556-3560.

S. Stipurin, T. Strassner, J. Organomet. Chem. 2023, 1000, 122785.

Y. Unger, D. Meyer, O. Molt, C. Schildknecht, I. Münster, G. Wagenblast, T. Strassner, Angew. Chem. Int. Ed. 2010, 49, 10214-10216.

A. A. T. Khan, H. B. Gobeze, T. Islam, H. D. Arman, K. S. Schanze, Dalton Trans. 2023, 52, 11535-11542.

T. Maganti, K. Venkatesan, ChemPlusChem 2022, 87, e202200014.

F. Wurl, S. Stipurin, J. I. Kollar, T. Strassner, Angew. Chem. Int. Ed. 2023, 62, e202301225.

H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 2012, 492, 234-238.

Y.-K. Qu, Q. Zheng, J. Fan, L.-S. Liao, Z.-Q. Jiang, Acc. Mater. Res. 2021, 2, 1261-1271.

H. Jiang, J. Jin, W. Wong, Adv. Funct. Mater. 2023, 33, 2306880.

G. Xia, C. Qu, Y. Zhu, J. Ye, K. Ye, Z. Zhang, Y. Wang, Angew. Chem. Int. Ed. 2021, 60, 9598-9603.

C. Poriel, J. Rault-Berthelot, Acc. Mater. Res. 2023, 4, 733-745.

J. Ma, M. Idris, T. Y. Li, D. S. M. Ravinson, T. Fleetham, J. Kim, P. I. Djurovich, S. R. Forrest, M. E. Thompson, Adv. Opt. Mater. 2022, 10, 2101530.

C. Brouillac, F. Kong, J. Rault-Berthelot, C. Quinton, Z. Jiang, C. Poriel, Adv. Mater. Technol. 2023, 8, 2300763.

L. Wang, W. Xiong, H. Tang, D. Cao, J. Mater. Chem. C 2019, 7, 9102-9111.

X.-Y. Liu, X. Tang, D. Zhao, B. Song, L. Ding, J. Fan, L.-S. Liao, Org. Electron. 2018, 61, 70-77.

S. L. McFarlane, L. S. Coumont, D. G. Piercey, R. McDonald, J. G. C. Veinot, Macromol. 2008, 41, 7780-7782.

L.-H. Xie, F. Liu, C. Tang, X.-Y. Hou, Y.-R. Hua, Q.-L. Fan, W. Huang, Org. Lett. 2006, 8, 2787-2790.

J. Zhao, G.-H. Xie, C.-R. Yin, L.-H. Xie, C.-M. Han, R.-F. Chen, H. Xu, M.-D. Yi, Z.-P. Deng, S.-F. Chen, Y. Zhao, S.-Y. Liu, W. Huang, Chem. Mater. 2011, 23, 5331-5339.

C.-S. Li, B.-Y. Ren, Y.-G. Sun, Resources Chemicals and Materials 2023, 2, 100-109.

I. Bulut, P. Chávez, S. Fall, S. Méry, B. Heinrich, J. Rault-Berthelot, C. Poriel, P. Lévêque, N. Leclerc, RSC Adv. 2016, 6, 25952-25959.

F.-C. Kong, Y.-L. Zhang, C. Quinton, N. Mcintosh, S.-Y. Yang, J. Rault-Berthelot, F. Lucas, C. Brouillac, O. Jeannin, J. Cornil, Z. Jiang, L.-S. Liao, C. Poriel, Angew. Chem. Int. Ed. 2022, 61, e202207204.

L. Sicard, C. Quinton, J.-D. Peltier, D. Tondelier, B. Geffroy, U. Biapo, R. Métivier, O. Jeannin, J. Rault-Berthelot, C. Poriel, Chem. Eur. J. 2017, 23, 7719-7727.

C. Poriel, L. Sicard, J. Rault-Berthelot, Chem. Commun. 2019, 55, 14238-14254.

C. Brouillac, W.-S. Shen, J. Rault-Berthelot, O. Jeannin, C. Quinton, Z.-Q. Jiang, C. Poriel, Mater. Chem. Front. 2022, 6, 1803-1813.

L. J. Sicard, H. Li, Q. Wang, X. Liu, O. Jeannin, J. Rault-Berthelot, L. Liao, Z. Jiang, C. Poriel, Angew. Chem. Int. Ed. 2019, 58, 3848-3853.

X. Tang, L.-S. Cui, H.-C. Li, A. J. Gillett, F. Auras, Y.-K. Qu, C. Zhong, S. T. E. Jones, Z.-Q. Jiang, R. H. Friend, L.-S. Liao, Nat. Mater. 2020, 19, 1332-1338.

V. van Pee, J.-P. Catinat, Preparation of a Fac-Isomer for a Tris Homoleptic Metal Complex, WO2012084219 A1, 2011.

L.-H. Xie, R. Zhu, Y. Qian, R.-R. Liu, S.-F. Chen, J. Lin, W. Huang, J. Phys. Chem. Lett. 2010, 1, 272-276.

J. H. Yao, C. Zhen, K. P. Loh, Z.-K. Chen, Tetrahedron 2008, 64, 10814-10820.

B.-Y. Ren, R.-D. Guo, D.-K. Zhong, C.-J. Ou, G. Xiong, X.-H. Zhao, Y.-G. Sun, M. Jurow, J. Kang, Y. Zhao, S.-B. Li, L.-X. You, L.-W. Wang, Y. Liu, W. Huang, Inorg. Chem. 2017, 56, 8397-8407.

B.-Y. Ren, J.-C. Yi, D.-K. Zhong, Y.-Z. Zhao, R.-D. Guo, Y.-G. Sheng, Y.-G. Sun, L.-H. Xie, W. Huang, Huaxue Xuebao 2020, 78, 56.

L. H.-Y. Lo, M.-C. Tang, S.-L. Lai, W.-L. Cheung, L.-K. Li, M. Ng, H.-T. Chan, M.-Y. Chan, V. W.-W. Yam, ACS Appl. Mater. Interfaces 2021, 13, 57673-57683.

T. Riesebeck, M.-S. Bertrams, S. Stipurin, K. Konowski, C. Kerzig, T. Strassner, Inorg. Chem. 2022, 61, 15499-15509.

T. Riesebeck, T. Strassner, Organometallics 2023, 42, 3275-3282.

R. Pittkowski, T. Strassner, Beilstein J. Org. Chem. 2018, 14, 664-671.

S. Stipurin, T. Strassner, Inorg. Chem. 2021, 60, 11200-11205.

S. Stipurin, T. Strassner, Eur. J. Inorg. Chem. 2022, 2022, e202200295.

S. Wang, Y. Fang, H. Wang, H. Gao, G. Jiang, J. Liu, Q. Xue, Y. Qi, M. Cao, B. Qiang, H. Zhang, Eur. J. Med. Chem. 2018, 159, 255-266.

M. J. Frisch, Gaussian 16, Revision A.03, 2016.

R. Dennington, T. A. Keith, J. M. Millam, GaussView, Version 6.0, Semichem Inc., Shawnee Mission, KS, 2016.

A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.

B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989, 157, 200-206.

P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.

S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211.

Lee, Yang, Parr, Phys. Rev. B 1988, 37, 785-789.

R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654.

A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639-5648.

M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654-3665.

S. Grimme, WIREs Comput Mol Sci 2011, 1, 211-228.

S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456-1465.

W. R. Wadt, P. J. Hay, J. Chem. Phys. 1985, 82, 284-298.

P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310.

P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 270-283.

L. E. Roy, P. J. Hay, R. L. Martin, J. Chem. Theory Comput. 2008, 4, 1029-1031.

R. L. Martin, J. Chem. Phys. 2003, 118, 4775-4777.

D. Drew, J. R. Doyle, A. G. Shaver, Inorg. Synth. 2007, 346-349.

S. Trofimenko, J. Am. Chem. Soc. 1967, 89, 3170-3177.

C. Zhang, P. Yang, Y. Yang, X. Huang, X.-J. Yang, B. Wu, Synth. Commun. 2008, 38, 2349-2356.

R. K. Harris, E. D. Becker, S. M. Cabral De Menezes, R. Goodfellow, P. Granger, Pure Appl. Chem. 2001, 73, 1795-1818.

Bruker AXS Inc., Bruker Crystallographic Suite APEX3, Madison, USA, 2017.

Bruker AXS Inc., Bruker Integration Engine SAINT, Madison, USA, 2017.

G. M. Sheldrick, SADABS Multi Scan Absorption, University of Goettingen, Goettingen, Germany 2016.

G. M. Sheldrick, Acta Crystallogr. C Struct. Chem. 2015, 71, 3-8.

G. M. Sheldrick, Acta Crystallogr. A 2015, 71, 3-8.

T. Hahn, Space-Group Symmetry, Kluwer Acad. Publ, Dordrecht, 1992.

G. M. Sheldrick, Acta Crystallogr. A 2008, 64, 112-122.

A. L. Spek, Acta Crystallogr. D 2009, 65, 148-155.

C. F. Macrae, I. Sovago, S. J. Cottrell, P. T. A. Galek, P. McCabe, E. Pidcock, M. Platings, G. P. Shields, J. S. Stevens, M. Towler, P. A. Wood, J. Appl. Crystallogr. 2020, 53, 226-235.

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, Williams, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian 16, Revision A.03, Wallingford, CT, 2016.

R. Dennington, T. A. Keith, J. M. Millam, GaussianView, Version 6.0, Semichem Inc., Shawnee Mission, KS, 2016.

Chemcraft - graphical software for visualization of quantum chemistry computations. Version 1.8, build 648. https://www.chemcraftprog.com (accessed Aug, 2023).