Design of bond-cleavage-induced intramolecular charge transfer emission with dibenzoboroles and their application to ratiometric sensors for discriminating chain lengths of alkanes

Matsumoto, Takuya; Takamine, Hirofumi; Tanaka, Kazuo; Chujo, Yoshiki

doi:10.1039/c7qm00350a

Cited by 51 publications

(48 citation statements)

References 44 publications

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“…Furthermore,w em easured the PL spectra of 3-Ph in various alkanes to investigate the effect of solvent viscosity.T he higher the viscosity,t he lower the relative intensity of the longer-wavelength emission (Figure S14). These results imply that the structural relaxation toward the planarization was impeded by PMMA or aviscous solvent matrix in the S 1 state.W ee stimate the activation energy (DE a )o ft he structural relaxation from the Franck-Condon state to the relaxed singlet state by the Stevens-Ban plot [21] of 3-Ph in 2-methyltetrahydrofuran ( Figure S15). The PL spectra of 3-Ph were measured from 145 Kto300 K, and the estimated DE a was 3.2 kJ mol À1 ,m eaning that the structural relaxation in the S 1 state can occur at room temperature.…”

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confidence: 99%

Dibenzoarsepins: Planarization of 8π‐Electron System in the Lowest Singlet Excited State

et al. 2019

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Dibenzo[b,f]arsepins possessing severely distorted cores compared to those of other heteropins were synthesized. These derivatives exhibited dual photoluminescence in the green-to-red region (500-700 nm) and the near-ultraviolet region (< 380 nm), whichcould be attributed to the planarization of the arsepin core in the lowest singlet excited (S 1 )s tate. The computational approach for the assessment of the aromatic indices revealed that the dibenzoarsepins studied show aromaticity (8p system) in the S 1 states in line with Bairdsrule.The lone pair electrons of the arsenic atoms play ac rucial role in the aromaticity in the S 1 states.

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confidence: 99%

Dibenzoarsepins: Planarization of 8π‐Electron System in the Lowest Singlet Excited State

et al. 2019

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“…The temperature dependency of the dual emission properties would provide mechanistic information. In addition, the dual emission properties are useful for realizing luminescent chromic materials toward environmental changes such as temperature, although emission efficiencies in the solution were small [ 54 ]. Therefore, we measured the PL spectra at various temperatures in the octane solution ( Figure 4 ).…”

Section: Resultsmentioning

confidence: 99%

Enhancement of Aggregation-Induced Emission by Introducing Multiple o-Carborane Substitutions into Triphenylamine

et al. 2017

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The enhancement of aggregation-induced emission (AIE) is presented on the basis of the strategy for improving solid-state luminescence by employing multiple o-carborane substituents. We synthesized the modified triphenylamines with various numbers of o-carborane units and compared their optical properties. From the optical measurements, the emission bands from the twisted intramolecular charge transfer (TICT) state were obtained from the modified triphenylamines. It was notable that emission efficiencies of the multi-substituted triphenylamines including two or three o-carborane units were enhanced 6- to 8-fold compared to those of the mono-substituted triphenylamine. According to mechanistic studies, it was proposed that the single o-carborane substitution can load the AIE property via the TICT mechanism. It was revealed that the additional o-carborane units contribute to improving solid-state emission by suppressing aggregation-caused quenching (ACQ). Subsequently, intense AIEs were obtained. This paper presents a new role of the o-carborane substituent in the enhancement of AIEs.

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“…Recently, the ICT process was explored for the development of WLE materials . Molecules that consist of electron donor (D) and electron acceptor (A) units connected through a single bond are well‐known ICT probes .…”

Section: Panchromatic Emission Through Charge Transfermentioning

confidence: 99%

“…In this view, excited‐state intramolecular proton transfer (ESIPT), the variation of monomer‐excimer emission, intramolecular charge transfer (ICT), etc. are the different photophysical processes used to achieve panchromatic emission . In addition, the presence of external stimuli like pH and heat can also affect the photophysics of an organic emitter in the ground and the excited state, leading to tunable emission .…”

Section: Introductionmentioning

confidence: 99%

Molecular Engineering Approaches Towards All‐Organic White Light Emitting Materials

Kundu

Pallavi

et al. 2020

Chemistry A European J

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White light emitting (WLE) materials are of increasing interesto wing to their promising applicationsi na rtificial lighting, display devices, molecular sensors, and switches.I n this context,o rganic WLE materials cater to the interesto f the scientific community owing to their promising features like color purity,l ong-term stability,s olutionp rocessability, cost-effectiveness,a nd low toxicity.T he typical methodf or the generation of white light is to combine three primary (red, green, and blue) or the two complementary (e.g., yellow and blue or red and cyan) emissive units covering the whole visible spectralw indow (400-800 nm). The judicious choice of molecular buildingb locks and connecting them through either strong covalentb onds or assembling through weakn oncovalent interactions are the key to achieve enhanced emissions panning the entire visible region.In the present review article, moleculare ngineering approaches for the development of all-organic WLE materials are analyzed in view of different photophysical processes like fluorescencer esonance energy transfer (FRET), excitedstate intramolecular protont ransfer (ESIPT), charget ransfer (CT), monomer-excimer emission, triplet-state harvesting, etc. The key aspect of tuning the molecular fluorescence under the influence of pH, heat, and host-guest interactions is also discussed. The white light emission obtained from small organic molecules to supramolecular assemblies is presented,i ncluding polymers, micelles,a nd also employing covalent organic frameworks. The state-of-the-art knowledge in the field of organic WLE materials, challenges, and future scope are delineated.

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Design of bond-cleavage-induced intramolecular charge transfer emission with dibenzoboroles and their application to ratiometric sensors for discriminating chain lengths of alkanes

Abstract: Dibenzoboroles with emission from the bond-cleavage-induced ICT was reported.

Cited by 51 publications

References 44 publications

Dibenzoarsepins: Planarization of 8π‐Electron System in the Lowest Singlet Excited State

Dibenzoarsepins: Planarization of 8π‐Electron System in the Lowest Singlet Excited State

Enhancement of Aggregation-Induced Emission by Introducing Multiple o-Carborane Substitutions into Triphenylamine

Molecular Engineering Approaches Towards All‐Organic White Light Emitting Materials

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