Resonance energy transfer-enhanced rhodamine–styryl Bodipy dyad triplet photosensitizers

Ma, Jie; Yuan, Xiaolin; Küçüköz, Betül; Li, Shengfu; Zhang, Caishun; Majumdar, Poulomi; Karatay, Ahmet; Li, Xiaohuan; Yağlıoğlu, H. Gül; Elmalı, Ayhan; Zhao, Jianzhang; Hayvalı, Mustafa

doi:10.1039/c3tc32456g

Cited by 52 publications

(50 citation statements)

References 88 publications

(146 reference statements)

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“…[d] Maximum emission wavelength. [e] Fluorescence quantum yields in toluene, diiodo‐styrylBODIPY ( Φ F =0.11 in toluene) was used as standard . [f] Fluorescence lifetime.…”

Section: Resultsmentioning

confidence: 97%

“…[g] Measured by nanosecond transient absorption ( c= 5.0×10 −6 m ). [h] Singlet oxygen quantum yield in toluene, diiodo‐BODIPY ( Φ Δ =0.85 in toluene) and Methylene Blue ( Φ Δ =0.57 in DCM) were used as standards . [i] Triplet state quantum yields in toluene, diiodo‐BODIPY was used as standard ( Φ T =0.88 in toluene) .…”

Section: Resultsmentioning

confidence: 97%

“…The fast decay component (t 1 = 0.4 ns) is attributed to the EISC process, which is in good agreement with the femtosecond [h] Singlet oxygen quantumy ieldi nt oluene,d iiodo-BODIPY (F D = 0.85 in toluene) andM ethylene Blue( F D = 0.57 in DCM)w ereu sed as standards. [61,62] [i]Triplet state quantum yields in toluene, diiodo-BODIPY was used as standard (F T = 0.88 in toluene). [62] Determined by nanosecondt ransienta bsorptions pectroscopy.…”

Section: Uv/vis Absorption and Fluorescencespectramentioning

confidence: 99%

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Efficient Radical‐Enhanced Intersystem Crossing in an NDI‐TEMPO Dyad: Photophysics, Electron Spin Polarization, and Application in Photodynamic Therapy

Wang

Gao

Hussain

et al. 2018

Chemistry A European J

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A compact naphthalenediimide (NDI)–2,2,6,6‐tetramethylpiperidinyloxy (TEMPO) dyad has been prepared with the aim of studying radical‐enhanced intersystem crossing (EISC) and the formation of high spin states as well as electron spin polarization (ESP) dynamics. Compared with the previously reported radical–chromophore dyads, the present system shows a very high triplet state quantum yield (ΦT=74 %), a long‐lived triplet state (τT=8.7 μs), fast EISC (1/kEISC=338 ps), and absorption in the red spectral region. Time‐resolved electron paramagnetic resonance (TREPR) spectroscopy showed that, upon photoexcitation in fluid solution at room temperature, the D0 state of the TEMPO moiety produces strong emissive (E) polarization owing to the quenching of the excited singlet state of NDI by the radical moiety (electron exchange J>0). The emissive polarization then inverts into absorptive (A) polarization within about 3 μs, and then relaxes to a thermal equilibrium while quenching the triplet state of NDI. The formation and decay of the quartet state were also observed. The dyad was used as a three‐spin triplet photosensitizer for triplet–triplet annihilation upconversion (quantum yield ΦUC=2.6 %). Remarkably, when encapsulated into liposomes, the red‐light‐absorbing dyad–liposomes show good biocompatibility and excellent photodynamic therapy efficiency (phototoxicity EC50=3.22 μm), and therefore is a promising candidate for future less toxic and multifunctional photodynamic therapeutic reagents.

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“…[d] Maximum emission wavelength. [e] Fluorescence quantum yields in toluene, diiodo‐styrylBODIPY ( Φ F =0.11 in toluene) was used as standard . [f] Fluorescence lifetime.…”

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 97%

Section: Uv/vis Absorption and Fluorescencespectramentioning

confidence: 99%

See 1 more Smart Citation

Efficient Radical‐Enhanced Intersystem Crossing in an NDI‐TEMPO Dyad: Photophysics, Electron Spin Polarization, and Application in Photodynamic Therapy

Wang

Gao

Hussain

et al. 2018

Chemistry A European J

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“…One of the major limitations of these triplet PSs is the short T 1 lifetime (typically ∼83 µs). In order to address this challenge, enhanced triplet‐state PSs with long‐lived T 1 were developed by Zhao and colleagues , comprising two organic PSs that show resonance energy transfer. These have a strong broadband visible absorption spectrum and predictable inter‐system crossing, which are crucial for potential PDT applications.…”

Section: Strategies For Enhanced Photosensitized 1o2 Generationmentioning

confidence: 99%

Photosensitized singlet oxygen generation and detection: Recent advances and future perspectives in cancer photodynamic therapy

Lin

et al. 2016

Journal of Biophotonics

162

122

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Photodynamic therapy (PDT) uses photosensitizers and visible light in combination with molecular oxygen to produce reactive oxygen species (ROS) that kill malignant cells by apoptosis and/or necrosis, shut down the tumor microvasculature and stimulate the host immune system. The excited singlet state of oxygen ( 1 O 2 ) is recognized to be the main cytotoxic ROS generated during PDT for the majority of photosensitizers used clinically and for many investigational new agents, so that maximizing its production within tumor cells and tissues can improve the therapeutic response, and several emerging and novel approaches for this are summarized. Quantitative techniques for 1 O 2 production measurement during photosensitization are also of immense importance of value for both preclinical research and future clinical practice. In this review, emerging strategies for enhanced photosensitized 1 O 2 generation are introduced, while recent advances in direct detection and imaging of 1 O 2 luminescence are summarized. In addition, the correlation between cumulative 1 O 2 luminescence and PDT efficiency will be highlighted. Meanwhile, the validation of 1 O 2 luminescence dosimetry for PDT application is also considered. This review concludes with a discussion on future demands of 1 O 2 luminescence detection for PDT dosimetry, with particular emphasis on clinical translation.Eye-catching color image for graphical abstract.

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“…The dihydropyrrolo[2,1-a]isoquinoline skeleton can be constructed in two different ways. The first way is annelation of a pyrrole ring to an isoquiniline fragment (Ma et al, 2014;Fujiya et al, 2016;Nekkanti et al, 2016). The second one, in contrast, is annelation of an isoquiniline fragment to pyrrole derivatives (Sun et al, 2012;Wiest et al, 2016).…”

Section: Chemical Contextmentioning

confidence: 99%

A new approach to alkaloid-like systems: synthesis and crystal structure of 1-(2-acetyl-11-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]pyrrolo[2,1-a]isoquinolin-1-yl)propan-2-one

et al. 2017

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Resonance energy transfer-enhanced rhodamine–styryl Bodipy dyad triplet photosensitizers

Abstract: Broadband visible light-absorbing triplet photosensitizers with rhodamine as the energy donor and styryl Bodipy as the energy acceptor/spin converter were prepared.

Cited by 52 publications

References 88 publications

Efficient Radical‐Enhanced Intersystem Crossing in an NDI‐TEMPO Dyad: Photophysics, Electron Spin Polarization, and Application in Photodynamic Therapy

Efficient Radical‐Enhanced Intersystem Crossing in an NDI‐TEMPO Dyad: Photophysics, Electron Spin Polarization, and Application in Photodynamic Therapy

Photosensitized singlet oxygen generation and detection: Recent advances and future perspectives in cancer photodynamic therapy

A new approach to alkaloid-like systems: synthesis and crystal structure of 1-(2-acetyl-11-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]pyrrolo[2,1-a]isoquinolin-1-yl)propan-2-one

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