“…[27][28] Silica gel for column chromatography was purchased from Sigma-Aldrich. 1 H, 13 C{ 1 H} and 19 F{ 1 H} NMR spectra were recorded at 298 K on either Bruker AV500 spectrometer in deuterated solvents and the residual solvent peak was used as the internal reference. NMR spectra were calibrated to residual solvent signals.…”
Section: Methodsmentioning
confidence: 99%
“…The overall synthetic strategy employed for the preparation of the target compounds 4 b-f and 5 b-f is depicted in Scheme 1. For all the intermediates and target compounds, 1 H, 13 C and (when applicable) 19 F NMR spectra are available in Figure S1 was tested as well, namely pathway B in Scheme 1. This second strategy involves Suzuki-Miyaura cross-coupling between boronic acids and bromo-derivatives (either 4 a or 5 a).…”
“…Imidazo[1,5‐ a ]pyridines and their coordination compounds are one of the most investigated ImPy isomers with optical properties [6–15] . Instead, design and investigation of luminophores containing the parental imidazo[1,2‐ a ]pyridine derivatives have been limited to date.…”
Ten novel small‐molecule fluorophores containing two electron‐accepting imidazo[1,2‐a]pyridine (ImPy) units are presented. Each ImPy core is functionalized at its C6 position with groups featuring either electron accepting (A) or donating (D) properties, thus providing emitters with general structure X−ImPy−Y−ImPy−X (X=either A or D; Y=phenyl or pyridine). The molecules bear either a phenyl (series 4) or a pyridine (series 5) π bridge that connects the two ImPys via meta (phenyl) or 2,6‐ (pyridine) positions, yielding an overall V‐shaped architecture. The final compounds are synthetized straightforwardly by condensation between substituted 2‐aminopyridines and α‐halocarbonyl derivatives. All the compounds display intense photoluminescence with quantum yield (PLQY) in the range of 0.17–0.51. Remarkably, substituent effect enables tuning the emission from near‐UV to (deep‐)blue region while keeping Commission Internationale de l’Éclairage (CIE) y coordinate ≤0.07. The emitting excited state is characterized by a few nanoseconds lifetime and high radiative rate constant, and its nature is modulated from pure π‐π* to intramolecular charge transfer (ICT) by the electronic properties of the peripheral X substituent. This is further corroborated by the nature of the frontier orbitals and vertical electronic excitations computed at (time‐dependent) density functional level of theory (TD‐)DFT. Finally, this study enlarges the palette of bright deep‐blue emitters based on the interesting ImPy scaffolds in view of their potential application as photo‐functional materials in optoelectronics.
“…[27][28] Silica gel for column chromatography was purchased from Sigma-Aldrich. 1 H, 13 C{ 1 H} and 19 F{ 1 H} NMR spectra were recorded at 298 K on either Bruker AV500 spectrometer in deuterated solvents and the residual solvent peak was used as the internal reference. NMR spectra were calibrated to residual solvent signals.…”
Section: Methodsmentioning
confidence: 99%
“…The overall synthetic strategy employed for the preparation of the target compounds 4 b-f and 5 b-f is depicted in Scheme 1. For all the intermediates and target compounds, 1 H, 13 C and (when applicable) 19 F NMR spectra are available in Figure S1 was tested as well, namely pathway B in Scheme 1. This second strategy involves Suzuki-Miyaura cross-coupling between boronic acids and bromo-derivatives (either 4 a or 5 a).…”
“…Imidazo[1,5‐ a ]pyridines and their coordination compounds are one of the most investigated ImPy isomers with optical properties [6–15] . Instead, design and investigation of luminophores containing the parental imidazo[1,2‐ a ]pyridine derivatives have been limited to date.…”
Ten novel small‐molecule fluorophores containing two electron‐accepting imidazo[1,2‐a]pyridine (ImPy) units are presented. Each ImPy core is functionalized at its C6 position with groups featuring either electron accepting (A) or donating (D) properties, thus providing emitters with general structure X−ImPy−Y−ImPy−X (X=either A or D; Y=phenyl or pyridine). The molecules bear either a phenyl (series 4) or a pyridine (series 5) π bridge that connects the two ImPys via meta (phenyl) or 2,6‐ (pyridine) positions, yielding an overall V‐shaped architecture. The final compounds are synthetized straightforwardly by condensation between substituted 2‐aminopyridines and α‐halocarbonyl derivatives. All the compounds display intense photoluminescence with quantum yield (PLQY) in the range of 0.17–0.51. Remarkably, substituent effect enables tuning the emission from near‐UV to (deep‐)blue region while keeping Commission Internationale de l’Éclairage (CIE) y coordinate ≤0.07. The emitting excited state is characterized by a few nanoseconds lifetime and high radiative rate constant, and its nature is modulated from pure π‐π* to intramolecular charge transfer (ICT) by the electronic properties of the peripheral X substituent. This is further corroborated by the nature of the frontier orbitals and vertical electronic excitations computed at (time‐dependent) density functional level of theory (TD‐)DFT. Finally, this study enlarges the palette of bright deep‐blue emitters based on the interesting ImPy scaffolds in view of their potential application as photo‐functional materials in optoelectronics.
The tricarbonylrhenium complexes that incorporate a mesoionic carbene ligand represent an emerging and promising class of molecules, the solid-state optical properties of which have rarely been investigated. The aim of...
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