Supramolecular J-aggregates of aza-BODIPY by steric and π–π nteractions for NIR-II phototheranostics

Tian, Youliang; Yin, Dalong; Quan, Cong; Dang, Huiping; Teng, Changchang; Yan, Lifeng

doi:10.1039/d1tb02820k

Cited by 45 publications

(28 citation statements)

References 70 publications

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“…Moreover, the loading capacity of aza-BODIPY-mPEG was calculated to be 54 ± 9%, according to the % yield of the conjugate. The NPs showed NIR absorbance peaking at 842 nm with a 15 nm bathochromic shift compared with that of aza-BODIPY-A in DMSO, which is possibly attributed to the interaction of strong π–π stacking of aza-BODIPY molecules in the J -aggregation . However, these dye-based NPs did not exhibit any fluorescent signal, confirming nonradiative relaxation via photothermal effect (Figure S5).…”

Section: Resultsmentioning

confidence: 89%

“…The NPs showed NIR absorbance peaking at 842 nm with a 15 nm bathochromic shift compared with that of aza- BODIPY-A in DMSO, which is possibly attributed to the interaction of strong π−π stacking of aza-BODIPY molecules in the J-aggregation. 39 However, these dye-based NPs did not exhibit any fluorescent signal, confirming nonradiative relaxation via photothermal effect (Figure S5). This PTT phenomenon might occur due to the intramolecular charge transfer from an electron-donating group such as NMe 2 and NH 2 groups to the aza-BODIPY core acting as the electron-accepting part.…”

Section: Photophysical Properties Of Aza-bodipy Npsmentioning

confidence: 78%

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PEGylated Aza-BODIPY Nanoparticles for Photothermal Therapy

Kampaengsri

Chansaenpak

Yong

et al. 2022

ACS Appl. Bio Mater.

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Photothermal therapy is a promising treatment modality in the realm of cancer therapy. Photothermal nanomaterials that absorb and emit in the near-infrared range (750−900 nm) have drawn a lot of attention recently because of the deep penetration of NIR light in biological tissue. Most nanomaterials, however, are produced by encapsulating or altering the surface of a nanoplatform, which has limited loading capacity and long-term storage. Herein, we developed a stable polymer conjugated with aza-BODIPY that self-assembled to form nanoparticles (aza-BODIPY-mPEG) with better hydrophilicity and biocompatibility while retaining the dye's photothermal conversion characteristics. Aza-BODIPY-mPEG with a hydrodynamic size of around 170 nm exhibited great photostability and excellent photothermal therapy in vitro and in ovo. Aza-BODIPY-mPEG exhibits approximately 30% better anti-angiogenesis and antitumor activity against implanted xenograft human HCT116 tumor in the chick embryo compared to parent aza-BODIPY-A, altogether suggesting that aza-BODIPY-mPEG is a promising material for cancer photothermal therapy.

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Section: Resultsmentioning

confidence: 89%

Section: Photophysical Properties Of Aza-bodipy Npsmentioning

confidence: 78%

PEGylated Aza-BODIPY Nanoparticles for Photothermal Therapy

Kampaengsri

Chansaenpak

Yong

et al. 2022

ACS Appl. Bio Mater.

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“…In recent years, some research groups reported NBA-OPDs with a response wavelength above 700 nm by taking advantage of the red shift of thin-film absorption caused by the J-aggregation properties of organic dye molecules. − Based on this strategy, we screened some known organic dyes with J-aggregation properties, such as cyanine dyes, squaraine dyes, perylene dyes, metalloporphyrin dyes, aza-BODIPY dyes, merocyanine dyes, and PPCy dyes. − These molecules have the characteristics of the large conjugated and planar structure and strong intermolecular non-covalent bonds, thus leading to strong coupling between molecules in the aggregated state, which in turn results in absorption narrowing and red shift and enhancement of the carrier transport rate via two-dimensional percolation pathways for electrons and hole charge carriers . Thus, these unique properties are desirable for the fabrication of NBA-OPDs.…”

Section: Introductionmentioning

confidence: 99%

Tuning of Molecular Aggregation and Photoresponse of Narrow-band Organic Photodetectors

Zhao

Zhang

et al. 2023

ACS Appl. Electron. Mater.

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It is a great challenge to find suitable organic materials for developing narrow-band absorption organic photodetectors (NBA-OPDs) working in the deep-red and near-infrared spectral regions. In general, if dye molecules can form J-aggregates, their maximal absorption peak will red-shift and become narrower. In this work, a suitably structured pyrrolopyrrole cyanine (PPCy) with this unique property is realized for use in narrow-band photodetectors. It was found that the Coulomb and charge-transfer (CT) couplings of J-aggregates of PPCy can be tuned by the complexing boron group. Using poly[N,N′-bis(4-butylphenyl)-N,N′-diphenylbenzidine] (poly-TPD) as the donor and PPCy as the acceptor, the bulk heterojunction blends were prepared. The crystallinity and the crystal size of PPCy in the active layer can be changed by adjusting the weight ratio of the donor and the acceptor. Thus, the charge carriers' transportation in the device can be regulated. Furthermore, organic photodetectors with an adjustable narrow spectral response (full width at half-maximum, FWHM, 55−148 nm) in the 600−800 nm range have been prepared. In self-powered mode, the device's maximum specific detectivity (D*) is 2.1 × 10 13 jones, which is the largest value among the reported NBA-OPDs in this spectral range. Moreover, when the mass ratio of poly-TPD and PPCy-1 is 2:1, the device exhibits the narrowest FWHM of 55 nm, an ultrafast response speed with a rise time of 0.4 μs and a decay time of 0.8 μs, and the maximum linear dynamic range of 168 dB. This work paves the way to construct a high-performance NBA-OPD by tuning the molecular aggregation of PPCy.

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“…21,23,24 Aza-BODIPY probes have exhibited attractive properties, in terms of facile synthesis and chemical modifications, outstanding optical properties and excellent photostability. [25][26][27][28] However, few of them exhibit NIR-II emission capabilities. [29][30][31][32] Herein, we report the design and preparation of a new aza-BODIPY-derived agent named CB1 with extended π-conjugation and proper structural modifications (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%