Investigation of thermal and luminescent properties in 4,7-diphenylethynyl-2,1,3-benzothiadiazole systems

Aguiar, Leonardo de O.; Regis, Elias; Tuzimoto, Patricia; Girotto, Edivandro; Bechtold, Ivan H.; Gallardo, Hugo; Vieira, André A.

doi:10.1080/02678292.2017.1293854

Cited by 29 publications

(14 citation statements)

References 38 publications

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“…Compared with other donor–acceptor π-conjugated molecules, such a narrow Δ Eg el is usually only seen in highly-conjugated polymers [47,48,49,50]. The results reveal the potentially beneficial properties of benzselenadiazole-based conjugated materials, and these results are in good agreement with other research [51,52,53,54,55,56].…”

Section: Resultssupporting

confidence: 89%

The Effect of Acceptor Structure on Emission Color Tuning in Organic Semiconductors with D–π–A–π–D Structures

et al. 2019

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A series of novel donor–acceptor D–π–A–π–D compounds were synthesized and characterized in order to determine the influence of different acceptor units on their properties. The introduction of acceptor moieties had a direct impact on the HOMO and LUMO energy levels. Fluorescence spectra of compounds can be changed by the choice of an appropriate acceptor and were shifted from the green to the near-infrared part of spectra. Due to observed concentration induced emission quenching, the green exciplex type host was used to evaluate the potential of synthesized molecules as emitters in organic light emitting diodes (OLEDs).

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Section: Resultssupporting

confidence: 89%

The Effect of Acceptor Structure on Emission Color Tuning in Organic Semiconductors with D–π–A–π–D Structures

et al. 2019

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“…Please note that although several rod-shaped BTD-based nematic and smectic liquid crystals have been reported, to our knowledge, all of them exhibit a C 2 symmetry. 25,28,29…”

Section: Resultsmentioning

confidence: 99%

“…Because of these attractive properties, this molecule has been extensively incorporated as an active layer in electronic devices. 24−27 By symmetrical functionalization with two aryl groups endowed with flexible chains, several BTD-based nematic and smectic liquid crystals 28 have been synthesized and incorporated as an active layer in organic field effect transistors (OFETs) 25 or as highly dichroic fluorescent dyes for liquid crystal displays. 29 However, to our knowledge, asymmetric monoalkyl liquid crystalline BTD derivatives have not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent and Electroactive Monoalkyl BTD-Based Liquid Crystals with Tunable Self-Assembling and Electronic Properties

et al. 2018

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We report here on a series of redox active benzothiadiazole-based luminophores functionalized on one edge with a phenyl-nonyl substituent, which confers these molecules a rodlike shape and a tendency to self-assemble into layered superstructures. On the other edge, the molecules are endowed with different p-substituted phenyl rings, which allows the modulation of their redox and optical properties on the basis of the electronic nature of the terminal substituents. We have found that just one lateral alkyl chain is sufficient to induce mesomorphism in these molecules, which present nematic or smectic mesophases upon thermal treatment. Single-crystal analysis allows us to get an insight into the nature of the forces responsible for different supramolecular assemblies in these derivatives, and point to a strong contribution of the terminal groups in the different arrangements observed. The interesting redox and optical properties together with their self-assembling tendencies render these new materials interesting candidates for optoelectronics.

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“… In general, the π‐extend BTD‐based structures [56–58] are stable and no degradation is noted when these fluorophores are emitting light. The electron deficient character of the BTD core is important for the planning of new stable structures with efficient stabilizing processes [59–61] BTD derivatives typically display good to excellent thermal stabilities [62–64] The fluorescent BTD derivatives usually display large Stokes shifts, [65–67] thus avoiding undesired background interferences and the excitation light to be efficiently blocked from reaching the detector by using the proper filters. Long irradiation periods are typically possible with no fade off. Bright emissions with no notable blinking by naked the eye occur often. Good to excellent signal‐to‐noise ratios are commonly obtained in the bioimaging experiments. Most of the described fluorescent small organic BTDs proved to be capable of transposing the cellular membrane, with few exceptions.…”

Section: Featured Physicochemical Properties Of Btd Derivativesmentioning

confidence: 99%

Fluorescent Benzothiadiazole Derivatives as Fluorescence Imaging Dyes: A Decade of New Generation Probes

Neto

Corrêa

Spencer

2021

Chemistry A European J

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The current review describes advances in the use of fluorescent 2,1,3‐benzothiadiazole (BTD) derivatives after nearly one decade since the first description of bioimaging experiments using this class of fluorogenic dyes. The review describes the use of BTD‐containing fluorophores applied as, inter alia, bioprobes for imaging cell nuclei, mitochondria, lipid droplets, sensors, markers for proteins and related events, biological processes and activities, lysosomes, plasma membranes, multicellular models, and animals. A number of physicochemical and photophysical properties commonly observed for BTD fluorogenic structures are also described.

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Investigation of thermal and luminescent properties in 4,7-diphenylethynyl-2,1,3-benzothiadiazole systems

Cited by 29 publications

References 38 publications

The Effect of Acceptor Structure on Emission Color Tuning in Organic Semiconductors with D–π–A–π–D Structures

The Effect of Acceptor Structure on Emission Color Tuning in Organic Semiconductors with D–π–A–π–D Structures

Fluorescent and Electroactive Monoalkyl BTD-Based Liquid Crystals with Tunable Self-Assembling and Electronic Properties

Fluorescent Benzothiadiazole Derivatives as Fluorescence Imaging Dyes: A Decade of New Generation Probes

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