Study on TICT emission of TPE-BODIPY derivatives mediated by methyl group on BODIPY
TL;DR: A series of tetraphenylethene-borondipyrromethene derivatives with different numbers of methyl groups on BODIPY cores were designed and synthesized.
About: This article is published in Optical Materials.The article was published on 2018-07-01. It has received 22 citations till now. The article focuses on the topics: BODIPY & Methyl group.
Citations
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TL;DR: This review encompasses the recent advances of TPE based AIE-active luminophores and their potential applications in biomolecular science.
50 citations
TL;DR: In this paper, a simple tetraphenylethylene with two electron-rich methyloxy groups and two electron withdrawing cyano groups, which features both twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) properties, namely TPEOMeCN has been prepared.
Abstract: A simple D–π–A structured tetraphenylethylene with two electron-rich methyloxy groups and two electron withdrawing cyano groups, which features both twisted intramolecular charge-transfer (TICT) and aggregation-induced emission (AIE) properties, namely TPEOMeCN has been prepared. The emission of TPEOMeCN examined in various solvents is dependent on the polarities of solvents, which indicates the TICT character. The emission intensity of the compound also enhances with the increasing water fraction in H2O–DMSO mixtures, demonstrating the typical AIE property. Excitingly, the TICT and AIE emission could be observed separately or simultaneously by adjusting the water fraction or viscosity of the solvent. Encouragingly, the combined emission of the TPEOMeCN derived from this single molecule could be readily tuned via regulating the viscosity of the system, resulting in a broad emission peak which covers the visible spectrum (400–700 nm). This work provides a general strategy for designing molecules combining TICT emission and AIE for application as full-color emitters.
21 citations
TL;DR: A set of fluorene-capped pendant conjugated molecules (T-m and T-p), which consist of a triazine center with three carbazole substituents as the donor-acceptor (D-A) type pendant structure, were designed, synthesized, and investigated as gain media for organic semiconductor lasers as discussed by the authors.
Abstract: A set of fluorene-capped pendant conjugated molecules (T-m and T-p), which consist of a triazine center with three carbazole substituents as the donor-acceptor (D-A) type pendant structure, were designed, synthesized, and investigated as gain media for organic semiconductor lasers (OSLs). In particular, varying the capping positions of the fluorene units on the pendant core structures results in significantly different intramolecular charge transfer (ICT) properties, where T-m manifested depressed ICT characteristic and high fluorescence quantum yield. The lowest amplified spontaneous emission (ASE) threshold in neat films was recorded as 1.9 μJ cm-2 for T-m and 83.8 μJ cm-2 for T-p, which indicated that the depressed ICT characteristics in the case of T-m help to enhance the ASE properties. Remarkably, the ASE threshold remained almost unchanged and the ASE spectra showed very small shifts (within 1 nm) for T-m with film samples annealed up to 180 °C in open air. In contrast, its linear counterpart 2FEtCz-m showed a clearly increased ASE threshold upon annealing above 100 °C. The results suggest that the selective construction of conjugated pendant molecules with depressed ICT characteristics is beneficial for finely modulating the optical and electrical properties as well as improving the thermostability and photostability, which manifests the great potential as a robust gain media for OSLs.
17 citations
TL;DR: In this paper, two methods of the Hellmanne-Feynman theorem and the McRae equation were used to estimate the difference of the dipole moment between the excited state and the ground state.
16 citations
TL;DR: In this article, a completely planar organic compound, 5,7,12,14-tetraoxapentacene A-D-A triad with carbon-oxygen bonds, showed typical aggregation-caused quenching (ACQ) effect.
12 citations
References
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TL;DR: This critical review covers the advances made using the 4-bora-3a,4a-diaza-s-indacene (BODIPY) scaffold as a fluorophore in the design, synthesis and application of fluorescent indicators for pH, metal ions, anions, biomolecules, reactive oxygen species, reactive nitrogen species, redox potential, chemical reactions and various physical phenomena.
Abstract: This critical review covers the advances made using the 4-bora-3a,4a-diaza-s-indacene (BODIPY) scaffold as a fluorophore in the design, synthesis and application of fluorescent indicators for pH, metal ions, anions, biomolecules, reactive oxygen species, reactive nitrogen species, redox potential, chemical reactions and various physical phenomena. The sections of the review describing the criteria for rational design of fluorescent indicators and the mathematical expressions for analyzing spectrophotometric and fluorometric titrations are applicable to all fluorescent probes (206 references).
1,846 citations
TL;DR: This review focuses on classifying different types of long wavelength absorbing BODIPY dyes based on the wide range of structural modification methods that have been adopted, and on tabulating their spectral and photophysical properties.
Abstract: This review focuses on classifying different types of long wavelength absorbing BODIPY dyes based on the wide range of structural modification methods that have been adopted, and on tabulating their spectral and photophysical properties. The structure–property relationships are analyzed in depth with reference to molecular modeling calculations, so that the effectiveness of the different structural modification strategies for shifting the main BODIPY spectral bands to longer wavelengths can be readily compared, along with their effects on the fluorescence quantum yield (ΦF) values. This should facilitate the future rational design of red/NIR region BODIPY dyes for a wide range of different applications.
1,013 citations
TL;DR: Boron dipyrromethene (BODIPY) derivatives 1 and 2 consisting of donor and acceptor units with dual photoresponses to solvent polarity and luminogen aggregation are developed through taking advantage of twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) processes as discussed by the authors.
Abstract: Boron dipyrromethene (BODIPY) derivatives 1 and 2 consisting of donor and acceptor units with dual photoresponses to solvent polarity and luminogen aggregation are developed through taking advantage of twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) processes. In nonpolar solvents, the locally excited (LE) states of the BODIPY luminogens emit intense green lights. Increasing solvent polarity brings the luminogens from the LE state to the TICT state, causing a large bathochromic shift in the emission color but a dramatic decrease in the emission efficiency. The red emission is greatly boosted by aggregate formation or AIE effect: addition of large amounts of water into the solutions of 1 and 2 in the polar solvents causes the luminogens to aggregate supramolecularly and to emit efficiently. The emission can be enhanced by increasing solvent viscosity and decreasing solution temperature, indicating that the AIE effect is caused by the restriction of the intramolecular ro...
794 citations
TL;DR: The proposed methodology departs from the traditional single-parameter procedures for estimating nonspecific solvent effects by splitting them into a polarizability term and a dipolarity term, and is applied to understanding for the indole chromophore the feasible inversion of the electronic nature for the first electronic excited state due to solvent effects.
Abstract: This paper reports a methodology for analyzing the solvent effect from empirical measurements of solvent acidity (SA), basicity (SB), dipolarity (SdP), and polarizability (SP). The proposed methodology departs from the traditional single-parameter procedures for estimating nonspecific solvent effects by splitting them into a polarizability term and a dipolarity term. In this work, we examined the SA, SB, SP, and SdP values for 160 solvents, the gas phase (the absence of solvent) being the origin of these scales. As shown in this paper, this information allows one not only to accurately describe the solvent effect experienced by any solute—whether polar or nonpolar and exhibiting some or no specific interaction with the solvent—but also to understand the nature of the well-known solvent parameters ET(30), π*, S′, and SPP, which are frequently used to describe the overall nonspecific contribution of solvents in terms of a single parameter. The high potential of the proposed empirical methodology is illustra...
548 citations