Synthesis and Photophysical Properties of Monometallic C^C* Platinum(II) Formamidinate Complexes using Sterically Demanding Ligands.
Amidinate
Cyclometalated Complexes
N-Heterocyclic Carbenes
OLED
Platinum
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
22 May 2023
22 May 2023
Historique:
received:
24
01
2023
medline:
18
3
2023
pubmed:
18
3
2023
entrez:
17
3
2023
Statut:
ppublish
Résumé
A novel class of cyclometalated platinum(II) complexes-previously considered to be inaccessible-was synthesized by an improved synthetic route utilizing ligands predicted by density functional theory calculations. Based on a concise quantum chemical screening three model ligands with varying steric demand were chosen and a series of six photoluminescent C^C* cyclometalated platinum(II) formamidinate complexes was obtained. The least sterically demanding ligand led to a bimetallic complex in two isomeric forms, which could be separated and confirmed by the corresponding solid-state structures. Sterically more hindered amidinate ligands gave the monometallic complexes supporting the theoretical predictions. The monometallic complexes show a significant hypsochromic shift of the emission wavelength, explained by the loss of the metal-metal interactions. Depending on the cyclometalating ligand quantum yields up to 87 % with short decay times were found for this new class of phosphorescent green-blue to pure blue platinum(II) emitters.
Identifiants
pubmed: 36929218
doi: 10.1002/anie.202301225
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301225Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151-154.
H. W. Chen, J. H. Lee, B. Y. Lin, S. Chen, S. T. Wu, Light: Sci. Appl. 2018, 7, 17168.
J. H. Lee, C. H. Chen, P. H. Lee, H. Y. Lin, M. K. Leung, T. L. Chiu, C. F. Lin, J. Mater. Chem. C 2019, 7, 5874-5888.
G. Hong, X. Gan, C. Leonhardt, Z. Zhang, J. Seibert, J. M. Busch, S. Bräse, Adv. Mater. 2021, 33, 2005630.
“Transition Metal and Rare Earth Compounds III”: H. Yersin in Topics in Current Chemistry, Vol. 241, Springer, Berlin, 2012, pp. 1-26.
M. E. Thompson, MRS Bull. 2007, 32, 694-701.
H. Xu, R. Chen, Q. Sun, W. Lai, Q. Su, W. Huang, X. Liu, Chem. Soc. Rev. 2014, 43, 3259-3302.
M. Sarma, K. T. Wong, Chem. Rec. 2019, 19, 1667-1692.
S. Wang, H. Zhang, B. Zhang, Z. Xie, W. Y. Wong, Mater. Sci. Eng. R 2020, 140, 100547.
H.-Y. Park, A. Maheshwaran, C.-K. Moon, H. Lee, S. S. Reddy, V. G. Sree, J. Yoon, J. W. Kim, J. H. Kwon, J.-J. Kim, S.-H. Jin, Adv. Mater. 2020, 32, 2002120.
“Photochemistry and Photophysics of Coordination Compounds II”: L. Flamigni, A. Barbieri, C. Sabatini, B. Ventura, F. Barigelletti in Topics in Current Chemistry, Vol. 281 (Eds.: V. Balzani, S. Campagna), Springer, Berlin, 2007, pp. 143-203.
T.-Y. Li, J. Wu, Z.-G. Wu, Y.-X. Zheng, J.-L. Zuo, Y. Pan, Coord. Chem. Rev. 2018, 374, 55-92.
H. Shin, Y. H. Ha, H.-G. Kim, R. Kim, S.-K. Kwon, Y.-H. Kim, J.-J. Kim, Adv. Mater. 2019, 31, 1808102.
C. S. K. Mak, A. Hayer, S. I. Pascu, S. E. Watkins, A. B. Holmes, A. Köhler, R. H. Friend, Chem. Commun. 2005, 4708-4710.
M. S. Lowry, S. Bernhard, Chem. Eur. J. 2006, 12, 7970-7977.
P. Tao, X. Lü, G. Zhou, W. Y. Wong, Acc. Mater. Res. 2022, 3, 830-842.
C. Wu, M. Wang, K. N. Tong, M. Zhang, W. Li, Z. Xu, W. L. Zhang, Y. Wu, C. Yang, H. Y. Fu, et al., Adv. Opt. Mater. 2023, 11, 2201998.
B. Ma, P. I. Djurovich, S. Garon, B. Alleyne, M. E. Thompson, Adv. Funct. Mater. 2006, 16, 2438-2446.
M. Cocchi, J. Kalinowski, D. Virgili, J. A. G. Williams, Appl. Phys. Lett. 2008, 92, 113302.
M. Cocchi, D. Virgili, V. Fattori, D. L. Rochester, J. A. G. Williams, Adv. Funct. Mater. 2007, 17, 285-289.
S. J. Farley, D. L. Rochester, A. L. Thompson, J. A. K. Howard, J. A. G. Williams, Inorg. Chem. 2005, 44, 9690-9703.
P.-K. Chow, G. Cheng, G. S. M. Tong, W.-P. To, W.-L. Kwong, K.-H. Low, C.-C. Kowk, C. Ma, C.-M. Che, Angew. Chem. Int. Ed. 2015, 54, 2084-2089.
T. Fleetham, G. Li, J. Li, Adv. Mater. 2017, 29, 1601861.
H. Amouri, Chem. Rev. 2023, 123, 230-270.
Y. Chi, P.-T. Chou, Chem. Soc. Rev. 2010, 39, 638-655.
T. Strassner, Acc. Chem. Res. 2016, 49, 2680-2689.
T. Sajoto, P. I. Djurovich, A. Tamayo, M. Yousufuddin, R. Bau, M. E. Thompson, R. J. Holmes, S. R. Forrest, Inorg. Chem. 2005, 44, 7992-8003.
M. Elie, J.-L. Renaud, S. Gaillard, Polyhedron 2018, 140, 158-168.
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.
D. H. Kim, N. S. Cho, H.-Y. Oh, J. H. Yang, W. S. Jeon, J. S. Park, M. C. Suh, J. H. Kwon, Adv. Mater. 2011, 23, 2721-2726.
Y. Unger, D. Meyer, O. Molt, C. Schildknecht, I. Münster, G. Wagenblast, T. Strassner, Angew. Chem. Int. Ed. 2010, 49, 10214-10216.
J. Soellner, P. Pinter, S. Stipurin, T. Strassner, Angew. Chem. Int. Ed. 2021, 60, 3556-3560.
J. R. Berenguer, Á. -Díez, E. Lalinde, M. T. Moreno, S. Ruiz, S. Sánchez, Organometallics 2011, 30, 5776-5792.
F. Niedermair, K. Waich, S. Kappaun, T. Mayr, G. Trimmel, K. Mereiter, C. Slugovc, Inorg. Chim. Acta 2007, 360, 2767-2777.
J. Li, P. I. Djurovich, B. D. Alleyne, M. Yousufuddin, N. N. Ho, J. C. Thomas, J. C. Peters, R. Bau, M. E. Thompson, Inorg. Chem. 2005, 44, 1713-1727.
M. Zábranský, J. Soellner, F. Horký, I. Císařová, P. Štěpnička, T. Strassner, Eur. J. Inorg. Chem. 2019, 2284-2290.
J. Soellner, T. Strassner, Eur. J. Inorg. Chem. 2021, 601-604.
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. Li, G. Cheng, C. Ma, X. Guan, W.-M. Kwok, Y. Chen, W. Lu, C.-M. Che, Chem. Sci. 2013, 4, 2630-2644.
T. Fleetham, G. Li, L. Wen, J. Li, Adv. Mater. 2014, 26, 7116-7121.
T. Fleetham, G. Li, J. Li, ACS Appl. Mater. Interfaces 2015, 7, 16240-16246.
K. Tuong Ly, R.-W. Chen-Cheng, H.-W. Lin, Y.-J. Shiau, S.-H. Liu, P.-T. Chou, C.-S. Tsao, Y.-C. Huang, Y. Chi, Nat. Photonics 2017, 11, 63-68.
J. Sun, H. Ahn, S. Kang, S. B. Ko, D. Song, H. A. Um, S. Kim, Y. Lee, P. Jeon, S. H. Hwang, et al., Nat. Photonics 2022, 16, 212-218.
S. Stipurin, F. Wurl, T. Strassner, Organometallics 2022, 41, 313-320.
F. T. Edelmann, Advances in Organometallic Chemistry, Vol. 57 (Eds.: A. F. Hill, M. J. Fink), Academic Press, Oxford, 2008, pp. 183-352.
F. T. Edelmann, Chem. Soc. Rev. 2009, 38, 2253-2268.
P. C. Junk, M. L. Cole, Chem. Commun. 2007, 1579-1590.
J. A. R. Schmidt, J. Arnold, Chem. Commun. 1999, 2149-2150.
T. Clark, S. D. Robinson, J. Chem. Soc. Dalton Trans. 1993, 2827-2834.
S. Dagorne, I. A. Guzei, M. P. Coles, R. F. Jordan, J. Am. Chem. Soc. 2000, 122, 274-289.
M. P. Coles, D. C. Swenson, R. F. Jordan, V. G. Young, Organometallics 1997, 16, 5183-5194.
S. Bambirra, M. J. R. Brandsma, E. A. C. Brussee, A. Meetsma, B. Hessen, J. H. Teuben, Organometallics 2000, 19, 3197-3204.
Y. Liu, K. Ye, Y. Fan, W. Song, Y. Wang, Z. Hou, Chem. Commun. 2009, 3699-3701.
V. K. Rai, M. Nishiura, M. Takimoto, Z. Hou, J. Mater. Chem. C 2014, 2, 5317-5326.
H. Leopold, M. Tenne, A. Tronnier, S. Metz, I. Münster, G. Wagenblast, T. Strassner, Angew. Chem. Int. Ed. 2016, 55, 15779-15782.
P. Pinter, J. Soellner, T. Strassner, Eur. J. Inorg. Chem. 2021, 3104-3107.
S. Stipurin, T. Strassner, Chem. Eur. J. 2022, 28, e202202227.
B. Ma, J. Li, P. I. Djurovich, M. Yousufuddin, R. Bau, M. E. Thompson, J. Am. Chem. Soc. 2005, 127, 28-29.
S. Moon, S. Horiuchi, E. Sakuda, A. Ito, Y. Arikawa, K. Umakoshi, Inorg. Chim. Acta 2019, 493, 43-48.
L. Arnal, S. Fuertes, A. Martín, M. Baya, V. Sicilia, Chem. Eur. J. 2018, 24, 18743-18748.
P. Pinter, J. Soellner, T. Strassner, Organometallics 2021, 40, 557-563.
K.-W. Lo, G. S. M. Tong, G. Cheng, K.-H. Low, C.-M. Che, Angew. Chem. Int. Ed. 2022, 61, e202115515.
Deposition Numbers 2217246 (for 5), 2217247 (for 3-trans), and 2217248 (for 3-cis) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. Van De Streek, J. Appl. Crystallogr. 2006, 39, 453-457.
J. V. Lockard, A. A. Rachford, G. Smolentsev, A. B. Stickrath, X. Wang, X. Zhang, K. Atenkoffer, G. Jennings, A. Soldatov, A. L. Rheingold, F. N. Castellano, L. X. Chen, J. Phys. Chem. A 2010, 114, 12780-12787.
K. Haldrup, A. O. Dohn, M. L. Shelby, M. W. Mara, A. B. Stickrath, M. R. Harpham, J. Huang, X. Zhang, K. B. Møller, A. Chakraborty, F. N. Castellano, D. M. Tiede, L. X. Chen, J. Phys. Chem. A 2016, 120, 7475-7483.
V. Sicilia, J. Fornie, J. M. Casas, A. Martín, J. A. López, C. Larraz, P. Borja, C. Ovejero, D. Tordera, H. Bolink, Inorg. Chem. 2012, 51, 3427-3435.
W. Lu, M. C. W. Chan, N. Zhu, C.-M. Che, C. Li, Z. Hui, J. Am. Chem. Soc. 2004, 126, 7639-7651.
Chemcraft-graphical software for visualization of quantum chemistry computations. https://www.chemcraftprog.com.
B. W. D'Andrade, S. Datta, S. R. Forrest, P. I. Djurovich, E. Polikarpov, M. E. Thompson, Org. Electron. 2005, 6, 11-20.
P. I. Djurovich, E. I. Mayo, S. R. Forrest, M. E. Thompson, Org. Electron. 2009, 10, 515-520.