Substitution at boron in BODIPYs

Gapare, Rosinah Liandrah; Thompson, Alison

doi:10.1039/d2cc02362h

Cited by 11 publications

(7 citation statements)

References 80 publications

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“…In this case, the potassium cation assisted the substitution of the fluoride by the alkoxide generated in situ . 18,19 We can speculate that, in our case the copper cation would assist the substitution of both fluorides by water molecules or solvent molecules, in a similar way as the potassium cation or the Lewis acid, leading to the corresponding free-base dipyrrin. Finally, a conjugated addition of water at the meso position, probably also catalysed by the copper cation, would lead to compound 3 .…”

Section: Resultsmentioning

confidence: 76%

Colorimetric and fluorescent detection of synthetic cathinones in oral fluid with meso-aryl BODIPYs and Cu(ii)

et al. 2022

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Section: Resultsmentioning

confidence: 76%

Colorimetric and fluorescent detection of synthetic cathinones in oral fluid with meso-aryl BODIPYs and Cu(ii)

et al. 2022

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“…As shown in Supporting Information, Fig. S1 , dipyrrin ligands (2, 4, 6, 8 and 19) can be prepared by the reaction of 2,4-dimethyl pyrrole or 2-methyl pyrrole with aromatic aldehyde (1, 3, 5 or 18) [ 55 ]. The Zn–dipyrrin complexes Z-1 − Z-6 can be easily prepared by stirring the mixture of dipyrrin ligands and zinc acetate at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Earth-abundant Zn–dipyrrin chromophores for efficient CO2 photoreduction

Guo,

Zeng,

et al. 2024

National Science Review

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Developing strong sensitizing and earth-abundant antenna molecules are highly desirable for CO2 reduction through artificial photosynthesis. Herein, a library of Zn-dipyrrin complexes (Z-1−Z-6) were rationally designed via precisely controlling their molecular configuration to optimize strong sensitizing earth-abundant photosensitizers. Upon visible light excitation, their special geometry enables intramolecular charge transfer to induce charge transfer state, which was firstly demonstrated to accept electrons from electron donor. The resulting long-lived reduced photosensitizer was confirmed to trigger consecutive intermolecular electron transfers for boosting CO2-to-CO conversion. Remarkably, the earth-abundant catalytic system with Z-6 and Fe-catalyst exhibits outstanding performance with over 20 000 turnover number and 29.7% quantum yield, representing an excellent catalytic performance among the molecular catalytic systems, and much superior to that of noble-metal photosensitizer Ir(ppy)2(bpy)+ under the similar condition. Experimental and theoretical investigations comprehensively unveil the structure-activity relationship, opening up a new horizon to develop earth-abundant strong sensitizing chromophores for boosting artificial photosynthesis.

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“…π-Conjugated push–pull molecular systems have gained considerable interest in the scientific community due to their tunable optoelectronic properties and wide range of applications such as in organic field-effect transistors, nonlinear optics, photovoltaic devices, energy harvesting, bioimaging, sensors, and organic light-emitting diodes. − The optoelectronic properties and HOMO–LUMO gap of the π-conjugated chromophores can be altered by modifying the donor (D) or acceptor (A) unit or the π-linker between the D and A units. , 4,4-Difluoro-4-bora-3a,4a-diaza- s -indacene dyes, frequently known as BODIPY, have attracted a lot of attention in the last few decades because of their excellent chemical and photophysical properties including strong absorption, high fluorescence quantum yields and molar absorption coefficients, low toxicity, long fluorescence lifetime, as well as good photochemical stability. − The optoelectronic characteristics of the BODIPYs can be tuned by expanding the conjugation and incorporation of appropriate D/A groups at the meso and pyrrolic locations (α and β positions). − As a result, the BODIPY-based π-conjugated dyes have been extensively used in building fluorescent imaging agents, molecular switches, chemosensors, laser dyes, light-emitting devices, photosensitizers, and optoelectronic materials. − Noticeably, depending upon the peripheral substituents, the BODIPY unit can act as an electron donor or acceptor. − …”

Section: Introductionmentioning

confidence: 99%

Dimethylaniline-Tetracyanobutadiene and Dimethylaniline-Extended-Tetracyanobutadiene Functionalized BODIPYs Witnessing Ultrafast Charge Transfer

Yadav,

Kaswan,

Liyanage

et al. 2024

J. Phys. Chem. C

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A new series of donor−acceptor push−pull systems, BODIPYs 1−4, were designed and synthesized by the palladium-catalyzed Sonogashira crosscoupling and [2 + 2] cycloaddition-retroelectrocyclization reactions in good yields. To prepare BODIPY 3 and 4, BODIPY 2 was modified with strong electron acceptors, tetracyanoethylene and 7,7,8,8-tetracyanoquinodimethane, resulting in tetracyanobutadiene (TCBD) and cyclohexa-2,5-diene-1,4-diylidene-expanded-TCBD (DCNQ) functionalized BODIPY 3 and 4, respectively. The effects of electron donor N,N-dimethylaniline (NND) and acceptors TCBD and DCNQ on the photophysical and redox properties of the BODIPYs are explored. The push− pull BODIPYs 1−4 exhibit intramolecular charge transfer (ICT) bands at longer wavelengths due to strong D−A interactions. The redox properties of the BODIPYs 1−4 exhibit multiple redox waves due to redox-active NND, BODIPY, TCBD, and DCNQ moieties. The computational studies were performed at the B3LYP/6-31G (d,p) level to understand the molecular geometry and electronic structure of the push−pull BODIPYs. Incorporating a strong electron acceptor, DCNQ decreased the LUMO levels more than the TCBD unit. Femtosecond pump−probe studies were performed to witness the excited-state charge separation process in dichlorobenzene for the BODIPYs 1−4. Finally, the data were analyzed by global target analysis (GloTarAn) which revealed the lifetime of charge-separated states in the range of 45−160 ps in dichlorobenzene, signifying their potential use in energy harvesting and other optoelectronic applications.

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Substitution at boron in BODIPYs

Abstract: BODIPYs provide tunable electronic properties key to many applications. This article highlights structural modification at boron.

Cited by 11 publications

References 80 publications

Colorimetric and fluorescent detection of synthetic cathinones in oral fluid with meso-aryl BODIPYs and Cu(ii)

Colorimetric and fluorescent detection of synthetic cathinones in oral fluid with meso-aryl BODIPYs and Cu(ii)

Earth-abundant Zn–dipyrrin chromophores for efficient CO2 photoreduction

Dimethylaniline-Tetracyanobutadiene and Dimethylaniline-Extended-Tetracyanobutadiene Functionalized BODIPYs Witnessing Ultrafast Charge Transfer

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