Cyclometalated N-heterocyclic carbene iridium( iii ) complexes with naphthalimide chromophores: a novel class of phosphorescent heteroleptic compounds
| Autor: | Hani Amouri, Geoffrey Gontard, Antoine Groué, Pierre-Henri Lanoë, Filippo Monti, Marie-Noëlle Rager, Nicola Armaroli, Andrea Barbieri, Jonny Chan, Anny Jutand |
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| Přispěvatelé: | Département de Chimie Moléculaire (DCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640) (PASTEUR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Département de Chimie - ENS Paris, École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Service de Résonance Magnétique Nucléaire, Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL), Istituto per la Sintesi Organica e la Fotoreattività (ISOF-CNR), Consiglio Nazionale delle Ricerche (CNR), Gulliver (UMR 7083), Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), IRPPS-CNR, Salerno, Università degli Studi di Salerno (UNISA) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Iridium complexes
Denticity Phosphorescence 010405 organic chemistry Ligand chemistry.chemical_element Nuclear magnetic resonance spectroscopy Chromophore [CHIM.INOR]Chemical Sciences/Inorganic chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry Polymer chemistry Imidazole Moiety Iridium Carbene ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Dalton Transactions Dalton Transactions, Royal Society of Chemistry, 2018, 47 (10), pp.3440-3451. ⟨10.1039/C7DT04369D⟩ Dalton transactions (2003. Print) 47 (2018): 3440–3451. doi:10.1039/c7dt04369d info:cnr-pdr/source/autori:Lanoe, Pierre-Henri; Chan, Jonny; Groue, Antoine; Gontard, Geoffrey; Jutand, Anny; Rager, Marie-Noelle; Armaroli, Nicola; Monti, Filippo; Barbieri, Andrea; Amouri, Hani/titolo:Cyclometalated N-heterocyclic carbene iridium(III) complexes with naphthalimide chromophores: a novel class of phosphorescent heteroleptic compounds/doi:10.1039%2Fc7dt04369d/rivista:Dalton transactions (2003. Print)/anno:2018/pagina_da:3440/pagina_a:3451/intervallo_pagine:3440–3451/volume:47 |
| ISSN: | 1477-9226 1477-9234 |
| DOI: | 10.1039/C7DT04369D⟩ |
| Popis: | A series of cyclometalated N-heterocyclic carbene complexes of the general formula [Ir(CN)(2)(CC:)] has been prepared. Two sets of compounds were designed, those where (CC:) represents a bidentate naphthalimide-substituted imidazolylidene ligand and (CN) = ppy (3a), F2ppy (4a), bzq (5a) and those where (CC:) represents a naphthalimide-substituted benzimidazolylidene ligand and (CN) = ppy (3b), F2ppy (4b), bzq (5b). The naphthalimide-imidazole and naphthalimide-benzimidazole ligands 1a,b and the related imidazolium and benzimidazolium salts 2a, b were also prepared and fully characterized. The N-heterocyclic carbene Ir(III) complexes have been characterized by NMR spectroscopy, cyclic voltammetry and elemental analysis. Moreover, the molecular structures of one imidazolium salt and four Ir(III) complexes were determined by single-crystal X-ray diffraction. The structures provide us with valuable information, most notably the orientation of the naphthalimide chromophore with respect to the N-heterocyclic carbene moiety. All compounds are luminescent at room temperature and in a frozen solvent at 77 K, exhibiting a broad emission band that extends beyond 700 nm. The presence of the naphthalimide moiety changes the character of the lowest excited state from (MLCT)-M-3 to (LC)-L-3, as corroborated by DFT and TD-DFT calculations. Remarkably, replacing imidazole with a benzimidazole unit improves the quantum yields of these compounds by decreasing the k(nr) values which is an important feature for optimized emission performance. These studies provide valuable insights about a novel class of N-heterocyclic carbene-based luminescent complexes containing organic chromophores and affording metal complexes emitting across the red-NIR range. |
| Databáze: | OpenAIRE |
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