Near‐IR‐Absorbing Bis‐Donor Functionalized Aza‐BODIPY Derivatives: Synthesis and Photophysical Study by Using Transient Optical Spectroscopy

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(27)

Published: Feb. 7, 2024

Abstract A series of near‐IR absorbing 2,6‐diarylated BF 2 ‐chelated aza‐boron‐dipyrromethenes (aza‐BDPs) derivatives bearing different electron donors (benzene, naphthalene, phenanthrene, phenothiazine and carbazole) were designed synthesized. The effect donor substitutions on the photophysical properties was studied by steady‐state UV‐vis absorption fluorescence spectra, electrochemical, time‐resolved nanosecond transient (ns‐TA) spectroscopy theoretical computations. spectra AzaBDP‐PTZ AzaBDP‐CAR ( λ abs =710 nm in toluene) showed a bathochromic profile compared with reference AzaBDP‐Ph =685 toluene), indicating non‐negligible electronic interaction at ground state between acceptor moieties. Moreover, is almost completely quenched for / (fluorescence quantum yield, Φ F =0.2–0.7 % as (Φ =27 toluene). However, apparent intersystem crossing ability these compounds poor, based singlet oxygen yield Δ =0.3–1.5 %). ns‐TA spectral study typical Bodipy localized triplet features, short‐lived excited (τ T =53.2 μs) versus significantly long‐lived =114 observed under deaerated experimental conditions. These lifetimes are much longer than that obtained diiodoAzaBDP (intramolecular heavy atom effect, τ =1.5~7.2 μs). information useful molecular structure design photosensitizers, which usually desired. Theoretical computations displayed mainly AzaBDP core, moreover, it found HOMO/LUMO energy gap decreased after introducing moieties to skeleton reference.

Language: Английский

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Near-infrared BODIPY photosensitizers for two-photon excited singlet oxygen generation and tumor cell photodynamic therapy

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(27), P. 5569 - 5577

Published: Jan. 1, 2024

Synthesis of near-infrared photosensitizers, two-photon excitation singlet oxygen generation by Cz-BDPI in zebrafish, and simulated photodynamic therapy with A549 tumor cells.

Language: Английский

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Introducing of an Unexplored Aza-BODIPY Diradicaloids with 4-(2,6-Ditert-butyl)phenoxyl Radicals Located in 1,7-Positions of the Aza-BODIPY Core

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 27, 2024

We have prepared and characterized two diradicaloid systems 5a 5b that originated from the oxidation of a 1,7-(4-(2,6-di-tert-butyl)phenol)-substituted aza-BODIPY core. The diradicaloids were by large array experimental computational methods. diamagnetic closed-shell state was postulated as ground in solution solid-state with substantial thermal population originating both open-shell diradical triplet states observed at room temperature. Transient absorption spectroscopy indicates fast (<10 ps) excited deactivation pathways associated target compounds' character Variable-temperature 1H NMR spectra indicate solvent dependency 5b. could be stepwise reduced to mixed-valence radical-anion dianion upon consequent single-electron reductions. Similarly, deprotonated aza-BODIPYs can oxidized form. Both dianionic forms exhibit an intense NIR region. Density functional theory (DFT) time-dependent DFT calculations used explain transformations UV–Vis-NIR all compounds.

Language: Английский

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Development of n-Type Small-Molecule Acceptors for Low Dark Current Density and Fast Response Organic Photodetectors

ACS Applied Materials & Interfaces, Journal Year: 2023, Volume and Issue: unknown

Published: Nov. 30, 2023

Suppressing the dark current density (Jd) while maintaining sufficient charge transport is important for improving specific detectivity (D*) and dynamic characteristics of organic photodetectors (OPDs). In this study, we synthesized three novel small-molecule acceptors (SMAs) densely surrounded by insulating alkyl side chains to minimize Jd in OPDs. Introducing trialkylated N-annulated perylene diimide as a terminal moiety alkylated π-conjugated core structure was highly efficient suppressing devices, resulting an extremely low 4.60 × 10–11 A cm–2 10–100 times improved D* values devices. addition, SMAs with geometrically aligned backbone exhibited better intermolecular ordering blended films, 3–10 high responsivity (R) Outstanding OPD performances 8.09 1012 Jones, −3 dB cutoff frequency 205.2 kHz, rising response time 16 μs were achieved under 530 nm illumination photoconductive mode. Geometrically core-terminal are promising static properties

Language: Английский

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Remotely Modulating the Optical Properties of Organic Charge-Transfer Crystallites via Molecular Packing

The Journal of Physical Chemistry Letters, Journal Year: 2024, Volume and Issue: 15(34), P. 8676 - 8681

Published: Aug. 19, 2024

Organic charge-transfer complex (CTC) formation has emerged as an effective molecular engineering strategy for achieving the desired optical properties via intermolecular interactions. By synthesizing organic CTCs with carbazole-based electron donors and a 7,7,8,8-tetracyanoquinodimethane acceptor adopting linker located remotely from interface within donors, we were able to modulate near-infrared absorptive short-wavelength infrared emissive properties. Structural characterizations performed by using single-crystal X-ray diffraction confirmed that unique arrangements induced steric hindrance significantly influence electronic interactions between donor molecules, resulting in different photophysical Our findings offer improved understanding of interplay packing optoelectronic properties, providing foundation designing advanced materials applications.

Language: Английский

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High‐Performance Single‐Microplate Perovskite Photodetectors Based on Polyvinyl Alcohol Filled Planar Electrodes for Weak‐Light Imaging and Pixel Integration

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 17, 2024

Abstract Photoconductors featuring an individual micro/nano‐crystal as the photoactive channel hold great promise for next‐generation integrated optoelectronics. Meanwhile, gain aiming signal amplification without extra amplifier, fast response data transfer, and low dark current weak acquisition are highly desirable in optoelectronics, but inherent trade‐off traditional photoconductors. Herein, study demonstrates a single‐microplate MAPbI 3 photoconductor based on polyvinyl alcohol‐filled planar electrodes that can simultaneously achieve excellent performance these parameters. The superior be attributed to exquisite design of filling device gap with alcohol. This deep‐work‐function transparent alcohol not only passivate surface defects perovskite microplate by hydrogen bonding, also form heterojunction top perovskites induce depleted channel. Resultant photodetectors exhibit exceptional characteristics including ultra‐low noise‐equivalent power 0.19 fW Hz −1/2 , high specific detectivity 3.68 × 10 14 Jones, 3.2 µs, EQE‐bandwidth over 7 Hz, well stability. More importantly, photoconductors demonstrate ultra‐weak‐light imaging ability surpassing silicon counterparts. Furthermore, successful integration their pixels showcases promising prospect

Language: Английский

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Functionalized Aza-BODIPYs and Their Use in the Synthesis of Aza-BODIPY-Based Complex Systems

Synlett, Journal Year: 2023, Volume and Issue: 35(01), P. 55 - 83

Published: Aug. 17, 2023

Abstract In this account, we present syntheses of various functionalized aza-boron-dipyrromethene dyes (aza-BODIPYs) in which the functional groups are directly introduced at 2- or 6-positions aza-BODIPYs on aryl rings 1-, 3-, 5-, and 7-positions aza-BODIPYs. Some these have been used for synthesis aza-BODIPY-based energy-transfer cassettes light-harvesting complexes. 1 Introduction 2 Monofunctionalized Aza-BODIPYs 2.1 2-/6-Monofunctionalized 2.2 1-/3-/5-/7-Monofunctionalized 3 Difunctionalized Aza-BODIPYs. 3.1 2,6-Difunctionalized 3.2 3,5-Difunctionalized 3.3 1,7-Difunctionalized 4 Miscellaneous 5 Conclusion

Language: Английский

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Synthesis of thiophene-isoindigo receptor small molecules and its application in photodetectors

Journal of Physics Conference Series, Journal Year: 2024, Volume and Issue: 2730(1), P. 012013 - 012013

Published: June 1, 2024

Abstract Organic photodetectors (OPDs) have attracted wide attention from researchers on account of their characteristics such as easy to manufacture, low cost, lightweight, and flexible detectors. Many efforts been made improve the performance OPDs. Scientists many organic photodetectors. Among them, narrow-band-gap photoelectric functional materials with spectral response exhibit application prospects in detection. In this paper, a series thienoisoindigo receptor small molecules were synthesized by using thienoisoindigo, electron deficient terminal octyl cyanoacetate, 3-ethylrhodanine, 2-(3-ethyl-4-oxothiazolidine-2-ylidene) malonitrile units, 3-dodecylthiophene donor unit, The photodetector high detection rate is fabricated Bulk Heterojunction (BHJ) structure.

Language: Английский

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NIR II-responsive core–shell La₂O₂S:Er³⁺@La₂O₂S nanoparticles towards 1.5 μm photodetection

Journal of Materials Chemistry C, Journal Year: 2024, Volume and Issue: 12(30), P. 11386 - 11393

Published: Jan. 1, 2024

Schematic diagram of a 1550 nm near-infrared photoelectric detector based on MAPbI 3 /La 2 O S:2%Er 3+ @La S structure.

Language: Английский

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Modulation of the Electronic Structure and Optical Properties of VO₂ by Doping with X (X = Be, Mg, Al, Ga)

physica status solidi (b), Journal Year: 2024, Volume and Issue: 262(1)

Published: Aug. 26, 2024

Monoclinic VO 2 , a semiconductor with narrow bandgap, is highly suitable for infrared (IR) spectrum utilization. The electrical and optical properties of doped X are thoroughly examined. Specifically, Mg doping decreases the formation V–V dimers. presence 3 d orbitals V atoms s orbital atom leads to decrease in bandgap. This an absorption peak 10 4 mid‐infrared (mid‐IR) range, resulting that approximately ten times greater than pure . As result, it becomes simpler detect. Notably, responsiveness system IR light increases. significantly increases photocurrent density, 1000‐fold increase mid‐IR region tenfold near‐IR region. finding provides theoretical basis empirically exploring technology.

Language: Английский

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