Synthesis and Solvatofluorochromism Behaviors on Intramolecular Charge Transfer System of Novel D-π-A Dyes

Kim, Byung-Soon; Yu, Hyungwook; Son, Young-Α

doi:10.1080/15421406.2012.689733

Cited by 8 publications

(1 citation statement)

References 27 publications

(32 reference statements)

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“…Donor–acceptor (D–A) and acceptor–donor–acceptor (A–D–A) molecules that benefit from extended π-conjugation have been widely studied as a result of their unique properties such as charge transfer, − thermally activated delayed fluorescence, ,− and aggregation-induced emission (AIE) (Figure ). − This has led to their exploitation in a number of applications including organic light-emitting diodes, − organic photovoltaic materials, − and bioimaging. ,− In order for molecular materials to be utilized in the aforementioned applications, control over the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies is often required.…”

Section: Introductionmentioning

confidence: 99%

Tuning the Properties of Donor–Acceptor and Acceptor–Donor–Acceptor Boron Difluoride Hydrazones via Extended π-Conjugation

2022

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Molecular materials with π-conjugated donor–acceptor (D–A) and acceptor–donor–acceptor (A–D–A) electronic structures have received significant attention due to their usage in organic photovoltaic materials, in organic light-emitting diodes, and as biological imaging agents. Boron-containing molecular materials have been explored as electron-accepting units in compounds with D–A and A–D–A properties as they often exhibit unique and tunable optoelectronic and redox properties. Here, we utilize Stille cross-coupling chemistry to prepare a series of compounds with boron difluoride hydrazones (BODIHYs) as acceptors and benzene, thiophene, or 9,9-dihexylfluorene as donors. BODIHYs with D–A and A–D–A properties exhibited multiple reversible redox waves, solid-state emission with photoluminescence quantum yields up to 10%, and aggregation-induced emission (AIE). Optical band gaps (or highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) gaps) determined for these compounds (2.02–2.25 eV) agree well with those determined from cyclic voltammetry experiments (2.05–2.42 eV). The optoelectronic properties described herein are rationalized with density functional theory calculations that support the interpretation of the experimental findings. This work provides a foundation of understanding that will allow for the consideration of D–A and A–D–A BODIHYs to be incorporated into applications ( e.g. , organic electronics) where fine-tuning of band gaps is required.

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Section: Introductionmentioning

confidence: 99%

Tuning the Properties of Donor–Acceptor and Acceptor–Donor–Acceptor Boron Difluoride Hydrazones via Extended π-Conjugation

2022

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Dual Emission, Aggregation, and Redox Properties of Boron Difluoride Hydrazones Functionalized with Triphenylamines

et al. 2022

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π‐Conjugated molecular materials often exhibit interesting photoluminescence, redox, and optoelectronic properties that grant them utility as light‐harvesting materials in solar cells, as the emissive component of organic light‐emitting diodes, and as fluorescence sensors. Preparing dye conjugates by appending multiple dyes together to generate π‐conjugated molecules is a common strategy to enhance the properties of these materials as it often imparts traits that cannot be achieved by the building blocks independently. Herein, we report molecular materials that incorporate boron difluoride hydrazone (BODIHY) and triphenylamine (TPA) units that exhibit charge‐transfer character, dual‐emission, and aggregation‐induced emission. The title compounds have low‐energy absorption bands (λabs=455–493 nm) that are red‐shifted relative to BODIHYs with smaller π‐systems and exhibit dual‐emission in the solution, solid, and aggregate states. TPA–BODIHY (donor‐acceptor) conjugates show multiple reversible redox events and, in combination, the data presented herein indicate that there is electronic communication throughout the donor‐acceptor and acceptor‐donor‐acceptor π‐systems. These results are rationalized with the use of computational chemistry and solid‐state structural analysis. This study provides new opportunities for the design of molecular materials that are comprised of redox‐active photoluminescent dyes, including BODIHY, and their potential applications.

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Carbazole Dyes

Ziarani

Moradi

Lashgari

et al. 2018

Metal-Free Synthetic Organic Dyes

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Synthesis and Solvatofluorochromism Behaviors on Intramolecular Charge Transfer System of Novel D-π-A Dyes

Cited by 8 publications

References 27 publications

Tuning the Properties of Donor–Acceptor and Acceptor–Donor–Acceptor Boron Difluoride Hydrazones via Extended π-Conjugation

Tuning the Properties of Donor–Acceptor and Acceptor–Donor–Acceptor Boron Difluoride Hydrazones via Extended π-Conjugation

Dual Emission, Aggregation, and Redox Properties of Boron Difluoride Hydrazones Functionalized with Triphenylamines

Carbazole Dyes

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