Recent Advances in Photosensitizers of Heteroleptic Tris(cyclometalated) Iridium Complexes

doi:10.6023/cjoc202410017

Abstract

Cyclometalated iridium(III) complexes are widely used as photosensitizers in organic light-emitting diodes and as photocatalysts in solar energy conversion and organic chemical synthesis. These iridium complexes feature high intersystem crossing (ISC) efficiency and adjustable triplet excited state lifetimes. In recent years, they have gained significant attention in the field of triplet photosensitization. Effective molecular design strategies and principles have been developed to enhance the light absorption performance, luminescence quantum efficiency, and triplet excited state lifetime of iridium complexes. The molecular design strategies as well as the photophysical and photochemical properties associated with multi-pyridine heterocyclic metalized iridium(III) complexes [Ir(C^N)₂(N^N)]^＋ are discussed. It focuses on regulating properties such as visible light absorption and excited state lifetime, and reviews recent applications of iridium complexes in photocatalytic synthesis. Additionally, the article summarizes advancements in triplet-triplet annihilation photon upconversion (TTA-UC) and explores the correlations between the molecular structure and photosensitivity of heteroleptic tris(cyclometalated) iridium(III) complexes. This research provides insights for designing cyclometalated iridium(III) complexes with enhanced performance.

Key words: heteroleptic tris(cyclometalated) iridium complex, excited state, photocatalysis, triplet-triplet annihilation, photon upconversion

Cite this article

Qian Shi, Zhongyu Li, Han Li. Recent Advances in Photosensitizers of Heteroleptic Tris(cyclometalated) Iridium Complexes[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2389-2405.

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Fig. & Tab. 20

Figure 1. Molecular design strategies and potential applications of heteroleptic iridium complex IrIII(L1L1L2) Abs., S1, S2, Phos., IC, and ISC represent absorption, first singlet excited state, second singlet excited state, phosphorescence, internal conversion, and intersystem crossing, respectively.

Figure 2. (a) Structure of heteroleptic iridium complex [Ir(ppy)2(bpy)]＋ (Ir1); (b) Electronic configuration and the lowest-energy transitions of Ir(III) complexes; (c) Electronic transitions involving the excited states of LC, MLCT, and MC (MC levels are not emissive, GS represents ground state); (d) Absorption and emission spectra of Ir1 complex in acetonitrile[11a]

Figure 3. Tuning MLCT state energy through manipulation of frontier molecular orbitals

Figure 4. Fluorine substitution (F), cyano group (CN) substitution, TPA (triphenylamine) substitution, and the presence of N—H and O—H groups of heterometallic iridium(III) complexes IrIII(L1L1L2), along with the distribution of HOMO and LUMO orbitals

Photocatalyst	E_ox^a/V	E_red^a/V	E_0-0^b/eV	$E_{\operatorname{ox}}^{*}$^c/V	$E_{\operatorname{red}}^{*}$^c/V	Ref.
Ir1	＋0.87	－1.70	2.00	－1.13	＋0.22	[11a, 11e]
Ir2	＋1.51	－1.37	2.40	－0.89	＋1.03	[19f]
Ir3	＋1.49	－1.45	2.52	－1.04	＋1.07	[19f]
Ir4	＋0.83	－1.10	1.94	－1.11	＋0.84	[19e, 19h]
Ir6	＋0.87	－1.65	—^d	—^d	—^d	[22a]
Ir7	＋0.87	－1.33	—^d	—^d	—^d	[22b]
Ir8	＋0.91	－1.80	2.05	－1.14	＋0.25	[11a]
Ir9	＋1.31	－1.73	2.47	－1.16	＋0.74	[9, 11a]
Ir10	＋0.36	－2.60	2.28	－1.92	＋0.32	[2c, 11c]
Ir20	＋1.55	—^d	—^d	—^d	—^d	[8a]

Table 1. Redox potentials of selected cyclometalated iridium(III) photosensitizers

Figure 5. Examples of C^N and N^N ligands obtained through the addition of aromatic rings

Figure 6. Typical chromophores covalently linked to IrIII(L1L1L2) or directly chelated onto the Ir(III) center

Photo- catalyst	λ_em^max^a/nm	τ_T^b/μs	E_T/eV	Ref.
Ir1	602	0.275	2.29	[11e]
Ir2	557	0.224	2.23	[19g]
Ir3	540	—^c	2.30	[19f]
Ir4	750	0.027	—^c	[19h]
Ir5	666^d	2.3^d	2.07	[23c]
Ir6	588^e	0.1895^e	—^c	[22a]
Ir7	588^f	τ₁=0.0092^fτ₂=0.2156^f	—^c	[22b]
Ir7	611^g	τ₁=0.0354^gτ₂=0.1^g	—^c	[22b]
Ir8	581	0.557	2.13	[11c]
Ir9	470	2.3	2.61	[11a, 11c, 19f]
Ir10	518	1.9	2.39	[11c, 19f,]
Ir11	603^h	75.5^h	2.06	[25]
Ir12	608^h	73.6^h	2.06	[25]
Ir13	553/742^h	87.2^h	2.10	[24a]
Ir14	514^h	23.7^h	2.43	[24a]
Ir15	672/747^d,h	157.2^d,h	1.86	[23b]
Ir16	678/751^d,h	363.7^d,h	1.85	[23b]
Ir17	682/757^d,h	85.8^d,h	1.85	[23b]
Ir18	600/738^d,h	30.7^d,h	2.15	[23b]
Ir19	677^d	53.3^d	2.57	[23c]
Ir20	474^h	72.1^h	2.86	[8a]

Table 2. Photophysical properties of selected cyclometalated iridium(III) photosensitizers

Figure 7. Visible-light-induced Ir8 catalyzed Stphenson-Aza-Henry reaction

Figure 8. Oxidative α-amino functionalization

Figure 9. Visible-light-induced Ir8-catalyzed intramolecular cyclization reaction

Figure 10. Visible-light-induced Ir9 catalyzed dehydrogenation cross-coupling reaction

Figure 11. Photocatalytic intramolecular dearomative [2＋2] cycloaddition of indole derivatives induced by the energy transfer process (a) Indole derivatives tethered with olefins at the C3 position; (b) Indole derivatives tethered with olefins at the N1 position

Figure 12. Visible-light-enabled Ir9 catalyzed [2＋2] cycloaddition reaction

Figure 13. Visible light-induced Ir9 for energy-transfer-enabled decarboxylative functionalization reactions

Figure 14. Jablonski energy level diagram and energy transfer process of triplet-triplet annihilation upconversion

Figure 15. Structures of photosensitizer Ir10 and annihilators

Figure 16. Molecular structures of IrIII complexes (Ir11~Ir14) and triplet annihilators

Figure 17. Molecular structures of IrIII complexes (Ir5, Ir15~Ir19)

Figure 18. Molecular structures of IrIII complex Ir20 (a) and triplet annihilator PPO (b); (c) Fluorescence spectrum of Ir20 (red) and upconversion luminescence spectrum of the Ir20/PPO system excited at 447 nm (yellow) upon upconversion; (d) Photochemical reaction driven via the Ir20/PPO upconversion system

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杂环金属铱配合物光敏剂的研究进展