Synthesis, structure and photochemical properties of asymmetric NMe2-bearing aza-BODIPYs as novel photothermal agents

Li, Jinhui; Wang, Jie; Zhang, Dongxiang; Cui, Tianfang; Xu, Zhang-Run; Jiang, Xin‐Dong

doi:10.1016/j.dyepig.2022.110092

Cited by 13 publications

(6 citation statements)

References 57 publications

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“…[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. [26][27][28][29][30][31][32][33][34][35][36] Aza-BDPs have been used for various applications, such as solar cells, photosensitizers, chemosensors and bioimaging. [37][38][39][40][41][42][43][44][45][46] Our group is involved in the design and synthesis of donor-acceptor (D-A) architectures with NIR absorption for solution processed bulk heterojunction organic solar cells (BHJ-OSCs).…”

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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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%

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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“…[39][40][41][42][43][44][45][46][47][48][49][50] Compared to BODIPYs, [51][52][53][54][55] replacing the bridging carbon atom with the nitrogen atom can effectively reduce the overall HOMO-LUMO gap, resulting in a significant bathochromic shift in the absorption spectra. [56][57][58][59][60][61][62][63][64][65][66][67] Symmetric aza-BODIPYs were first synthesized by O'Shea group in 2002 (Fig. 1a).…”

Section: Introductionmentioning

confidence: 99%

Non-aryl substituted aza-BODIPYs at 1,7- or 3,5-sites: synthesis, structures, optical properties, and applications

2023

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“…Aza-BODIPY derivatives are known to be extensively employed in fluorescence imaging, phototherapy, photocatalysis, and others. [37][38][39][40][41] For blocking fluorescence, inducing intersystem crossing (ISC), and enhancing photothermal conversion, the skillful structural design of aza-BODIPYs is required, including photoinduced electron transfer (PET), 42,43 intramolecular charge transfer (ICT), 44,45 twisted intramolecular charge transfer (TICT), [46][47][48] or a rotor with the freely rotating groups. 49 Our group recently discovered that aza-BODIPY with tert-butyl groups at 1,7-or 3,5-sites is a novel molecule, and the rotating tert-butyl group caused non-radiative heat production in excited states, which is an intriguing approach for designing photothermal reagents (Fig.…”

Section: Introductionmentioning

confidence: 99%

Aza-BODIPY with two efficacious fragments for NIR light-driven photothermal therapy by triggering cancer cell apoptosis

Shao,

Gong,

Zhang

et al. 2023

J. Mater. Chem. B

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Synthesis, structure and photochemical properties of asymmetric NMe2-bearing aza-BODIPYs as novel photothermal agents

Cited by 13 publications

References 57 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

Non-aryl substituted aza-BODIPYs at 1,7- or 3,5-sites: synthesis, structures, optical properties, and applications

Aza-BODIPY with two efficacious fragments for NIR light-driven photothermal therapy by triggering cancer cell apoptosis

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