Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation: A novel molecular design of NIR-II dye

Yano, Masafumi; Inada, Yoshinori; Hayashi, Yasuhiko; Nakai, M.; Mitsudo, Koichi; Kashiwagi, Yukiyasu

doi:10.1016/j.dyepig.2021.109929

Cited by 8 publications

(3 citation statements)

References 29 publications

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“…[1][2][3][4][5][6][7][8] NIR-absorbing organic chromophores are becoming more widely used in a variety of applications, such as organic photovoltaics, organic light-emitting diodes, telecommunications, and photothermal therapy. [9][10][11][12][13][14][15][16][17] Aza-Boron-dipyrromethene (aza-BODIPY or aza-BDP) dyes are BDP derivatives that feature a nitrogen atom replaces the meso-carbon atom, which connects the two pyrrole rings. [18][19][20][21][22][23][24][25] Aza-BDP dyes possess favorable spectroscopic properties, including high molar absorption coefficients, intense NIR absorption and excellent photostability.…”

Section: Introductionmentioning

confidence: 99%

“…Near‐infrared (NIR) absorbing dyes are extensively used in bioimaging and environmental applications due to their ability to harvest NIR light, which offers excellent optical transparency, low auto‐fluorescence, minimal damage, and deep penetration into samples [1–8] . NIR‐absorbing organic chromophores are becoming more widely used in a variety of applications, such as organic photovoltaics, organic light‐emitting diodes, telecommunications, and photothermal therapy [9–17] …”

Section: Introductionmentioning

confidence: 99%

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

Pinjari,

Imran,

Dad

et al. 2024

Chemistry A European J

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A series of near‐IR absorbing 2,6‐diarylated BF2‐chelated aza‐boron‐dipyrromethenes (aza‐BDPs) derivatives bearing different electron donors (Benzene, naphthalene, phenanthrene, phenothiazine and carbazole) were designed and synthesized. The effect of different electron donor substitutions on the photophysical properties was studied by steady‐state UV‐vis absorption and fluorescence spectra, electrochemical, time‐resolved nanosecond transient absorption (ns‐TA) spectroscopy and theoretical computations. The UV−vis absorption spectra of AzaBDP‐PTZ and AzaBDP‐CAR (λabs = 710 nm in toluene) showed a bathochromic absorption profile compared with the reference AzaBDP‐Ph (λabs = 685 nm in toluene), indicating the non‐negligible electronic interaction at the ground state between donor and acceptor moieties. Moreover, the fluorescence is almost completely quenched for AzaBDP‐PTZ/AzaBDP‐CAR (fluorescence quantum yield, ΦF = 0.2−0.7% in toluene) as compared with the AzaBDP‐Ph (ΦF = 27% in toluene). However, the apparent intersystem crossing ability of these compounds is poor, based on the singlet oxygen quantum yield (ΦΔ = 0.3−1.5%). The ns‐TA spectral study showed typical Bodipy localized triplet state transient features, short‐lived excited triplet state for AzaBDP‐Ph (τT = 53.2 μs) versus significantly long‐lived triplet state for AzaBDP‐CAR (τT = 114 μs) was observed under deaerated experimental conditions. These information are useful for molecular structure design of triplet photosensitizers.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Pinjari,

Imran,

Dad

et al. 2024

Chemistry A European J

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show abstract

“…[13][14][15] Narrow bandgap organic compounds possess strong absorption and/or emission in near-infrared (NIR) region and are required for solar-energy-related applications, bio-imaging and medical applications. [16][17][18][19][20] Generally, organic molecules with narrow bandgaps can be designed by introducing of electron donating-accepting (D-A) structures and quinoid structures. 21,22 N-Type organic semiconductors are essential materials in OFETs and OSCs.…”

Section: Introductionmentioning

confidence: 99%

An n -Type All-Fused-Ring Molecule with Narrow Bandgap

Zhang

Miao

et al. 2023

CCS Chem

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All-fused-ring π-conjugated molecules have received great attention because of their unique electronic structures, low conformation disorder and excellent opto-electronic properties. Most of all-fused-ring molecules are p-type organic semiconductors and possess medium bandgaps. In this work, we design and synthesize an all-fused-ring molecule (FM1) with n-type property and narrow bandgap, which is a ten-fusedring system composing of one electron-deficient benzotriazole core, two electron-rich thienopyrrole bridging units and two electron-deficient malononitrile-functionalized end-cappers. FM1 exhibits low-lying HOMO/LUMO energy levels of −5.77 eV/−3.89 eV, high electron mobility of 6.0 × 10 −4 cm 2 V −1 s −1 , optical bandgap of 1.50 eV and maximum absorption wavelength of 769 nm. Because of the all-fused-ring skeleton, FM1 shows superior photo stability and chemical stability. We use FM1 as an electron acceptor and successfully construct organic solar cell (OSC) devices with a decent power conversion efficiency (PCE) of 10.8%. Most importantly, the intrinsic stability of FM1 leads to its excellent OSC device stability. After irradiation with simulated solar light for 16 hours, while control OSC device of the state-of-the-art small molecule electron acceptor shows 46% decrease of PCE, the unencapsulated OSC device of FM1 exhibits only 9% decrease of PCE.

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Diastereoselective Construction of CF₃‐Containing Bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s through 1,3‐Dipolar Cycloaddition

Niu

2022

Eur J Org Chem

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A new protocol to access CF 3 -containing bispiro[isoquinolonepyrrolidine-benzothiophenone]s was described. A series of 1,3dipoles were synthesized from isoquinolinetrione and CF 3 CH 2 NH 2 . In the presence of 10 mol% DABCO, the 1,3-dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up to 98 %) and diastereoselectivities (up to > 20 : 1 dr).

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Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation: A novel molecular design of NIR-II dye

Cited by 8 publications

References 29 publications

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

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

An n -Type All-Fused-Ring Molecule with Narrow Bandgap

Diastereoselective Construction of CF₃‐Containing Bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s through 1,3‐Dipolar Cycloaddition

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Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation: A novel molecular design of NIR-II dye

Cited by 8 publications

References 29 publications

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

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

An n -Type All-Fused-Ring Molecule with Narrow Bandgap

Diastereoselective Construction of CF3‐Containing Bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s through 1,3‐Dipolar Cycloaddition

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Product

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Diastereoselective Construction of CF₃‐Containing Bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s through 1,3‐Dipolar Cycloaddition