Cationic Organophosphorus Chromophores: A Diamond in the Rough among Ionic Dyes

Belyaev, Andrey; Chou, Pi‐Tai; Koshevoy, Igor O.

doi:10.1002/chem.202001853

Cited by 22 publications

(28 citation statements)

References 143 publications

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“…In this emerging field, herein, we aim at exploring the factors affecting the ESICT‐induced ion motion and photophysical features of emissive ion‐paired D−π−A + salts (π=−(C 6 H 4 ) x −) via a new series of phosphonium dyes with various branching CT chromophores. The strategy lies in the unique connectivity and accessible quaternization of the phosphorus atom, [11] which allow us to synthesize novel multipolar molecules (D−π−) n A + with variable number of and length of linear donor–acceptor arms, + PPh 4‐ n (−π−D) n ( n =1–4) and + PPh 2 (−π−D)(−π′−D). To probe the cationic effect, we also chemically alter the acceptor group by introducing the methyl group along the aromatic substituents in + PMePh 3‐ m (−π−D) m ( m =1, 3).…”

Section: Introductionmentioning

confidence: 99%

Multiple Emission of Phosphonium Fluorophores Harnessed by the Pathways of Photoinduced Counterion Migration

Koshevoy

Belyaev

et al. 2022

Angew Chem Int Ed

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In the emerging field of intramolecular charge transfer induced counterion migration, we report the new insights into photophysical features of luminescent donor-acceptor phosphonium dyes (DÀ πÀ ) n A + [X À ] (π = À (C 6 H 4 ) x À ). The unique connectivity of the phosphorus atom affords multipolar molecules with a variable number of arms and the electronic properties of the acceptor group. In the ion-paired form, the transition from dipolar to quadrupolar configuration enhances the low energy migration-induced band by providing the additional pathways for anion motion. The multipolar architecture, adjustable lengths of the π-spacers and the nature of counterions allow for efficient tuning of the emission and achieving nearly pure white light with quantum yields around 30 %. The methyl substituent at the phosphorus atom reduces the rate of ion migration and suppresses the red shifted bands, simultaneously improving total emission intensity. The results unveil the harnessing of the multiple emission of phosphonium fluorophores by anion migration via structure and branching of donor-acceptor arms.

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Section: Introductionmentioning

confidence: 99%

Multiple Emission of Phosphonium Fluorophores Harnessed by the Pathways of Photoinduced Counterion Migration

Koshevoy

Belyaev

et al. 2022

Angew Chem Int Ed

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“…Among the dyes used, the conjugated type accounts for more than 90%. [ 37,38 ] There are many varieties of conjugated cationic dyes, such as triarylmethane, oxazine, and polymethine structures. These materials can be directly used to fabricate sensory devices [ 39,40 ] and memory devices, [ 41 ] with the merits of a high molar absorbance coefficient, [ 42 ] large abundance, [ 43 ] and high environmental stability.…”

Section: Synthesis Of Iic Materialsmentioning

confidence: 99%

Ion‐in‐Conjugation: A Promising Concept for Multifunctional Organic Semiconductors

2022

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Most organic semiconductors (OSCs) consist of conjugated skeletons with flexible peripheral chains. Their weak intermolecular interactions from dispersion and induction forces result in environmental susceptibilities and are unsuitable for many multifunctional applications where direct exposure to external environments is unavoidable, such as gas absorption, chemical sensing, and catalysis. To exploit the advantages of inorganic semiconductors in OSCs, ion‐in‐conjugation (IIC) materials are proposed. An IIC material refers to any conjugated material (molecules, polymers, and crystals) in Kekule's structural formula containing stoichiometric ionic states in its conjugated backbone in the electronic ground state. In this review, the definitions, structures, synthesis, properties, and applications of IIC materials are described briefly. Four types of IIC material, including zwitterionic conjugated molecules/polymers, conjugated ionic dyes, π‐d conjugated molecules and polymers, and coordinatively doped polymers, are reported. Their applications in gas sensing, humidity sensing, resistive memory devices, and thermal/photo‐/electro‐catalysis are demonstrated. The challenges and opportunities for future research are also discussed. It is expected that this work will inspire the design of new organic electronic information materials.

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“…-clearly eclipse those of all-carbon architectures. [11][12][13][14][15][16][17][18][19][20] The synthesis of acenes; i. e. linearly-fused hexagonal carbon rings, and their derivatives have received a great deal of attention in the last decades. Since their first discovery by Clar in the 1930s, [21] pentacenes evolved from simple curiosities to become the hallmark of hole transporting semiconductors for organic field-effect transistors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Post‐Functionalization and Properties of Diphosphapentaarenes

Regulska

Hindenberg

Espineira-Gutierrez

et al. 2022

Chemistry A European J

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Linearly‐fused polyarenes are an important class of compounds with high relevance in materials science. While modifying the shape and size represents a common means to fine‐tune their properties, the precise placement of heteroatoms is a strategy that is receiving an increasing deal of attention to overcome the intrinsic limitations of all‐carbon structures. Thus, linearly‐fused diphosphaarenes recently emerged as a novel family of molecules with striking optoelectronic properties and outstanding stability. However, the properties of diphosphaarenes are far from being benchmarked. Herein, we report the synthesis, phosphorus post‐functionalization and properties of new diphosphapentaarene derivatives. We describe their synthetic limitations and unveil their potential for optoelectronic applications.

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Cationic Organophosphorus Chromophores: A Diamond in the Rough among Ionic Dyes

Cited by 22 publications

References 143 publications

Multiple Emission of Phosphonium Fluorophores Harnessed by the Pathways of Photoinduced Counterion Migration

Multiple Emission of Phosphonium Fluorophores Harnessed by the Pathways of Photoinduced Counterion Migration

Ion‐in‐Conjugation: A Promising Concept for Multifunctional Organic Semiconductors

Synthesis, Post‐Functionalization and Properties of Diphosphapentaarenes

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