Synthesis of a triphenylamine BODIPY photosensitizer with D–A configuration and its application in intracellular simulated photodynamic therapy

Wang, Lingfeng; Bai, Jin; Qian, Ying

doi:10.1039/c9nj04166d

Cited by 28 publications

(14 citation statements)

References 48 publications

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“…Due to these excellent photophysical characteristics, BODIPY dyes increase their potential using in different applications such as fluorescent labels for biomolecules and cellular imaging [11][12][13][14][15], light-emitting devices [16][17][18], drug delivery agents [19][20][21], photosensitizers [22][23][24], fluorescent switches [25], chemosensors [26][27][28][29], energy transfer cassettes [30][31][32][33], and solar cells [34][35][36][37]. In this chapter, general photophysical properties of BODIPY and aza-BODIPY derivatives and recent studies on the photophysical properties of these dyes are presented.…”

Section: Introductionmentioning

confidence: 99%

Photophysics of BODIPY Dyes: Recent Advances

Çetindere¹

2021

Photophysics, Photochemical and Substitution Reactions - Recent Advances

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BODIPY dyes are unique fluorophores that can be used in numerous application areas because of their interesting photophysical properties such as high molar absorptivity, tunable absorption and emission energies, and high fluorescence quantum yields. They show impressive photophysical property changes upon substitution of functional groups on the main core structure. Exchange of the meso-carbon on dipyrrin core with nitrogen produces an analog class of BODIPY called aza-BODIPY. Up to now, various kinds of BODIPY and aza-BODIPY derivatives have been developed and applied in science and industry. In this chapter, recent studies on photophysical properties of BODIPY derivatives are summarized.

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Section: Introductionmentioning

confidence: 99%

Photophysics of BODIPY Dyes: Recent Advances

Çetindere¹

2021

Photophysics, Photochemical and Substitution Reactions - Recent Advances

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“…N , N ′-chelate tetracoordinated organoboron compounds have been widely applied in various science and technology areas. For example, boron dipyrromethene derivatives (BODIPY) were developed in luminescent materials [ 1 , 2 , 3 , 4 , 5 ], dyes [ 6 , 7 , 8 , 9 ], photosensitizers [ 10 , 11 , 12 , 13 , 14 ], molecular switches [ 15 , 16 , 17 ], photodynamic therapy [ 18 , 19 , 20 , 21 , 22 ], molecular probes [ 23 , 24 , 25 , 26 ], and bioimaging [ 27 , 28 , 29 ]. In recent decades, N , N ′-chelate compounds become a popular topic and have gradually attracted the attention of scientists.…”

Section: Introductionmentioning

confidence: 99%

“…The data presented in this study are openly available in references [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , …”

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Recent Progress on Synthesis of N,N′-Chelate Organoboron Derivatives

et al. 2021

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N,N′-chelate organoboron compounds have been successfully applied in bioimaging, organic light-emitting diodes (OLEDs), functional polymer, photocatalyst, electroluminescent (EL) devices, and other science and technology areas. However, the concise and efficient synthetic methods become more and more significant for material science, biomedical research, or other practical science. Here, we summarized the organoboron-N,N′-chelate derivatives and showed the different routes of their syntheses. Traditional methods to synthesize N,N′-chelate organoboron compounds were mainly using bidentate ligand containing nitrogen reacting with trivalent boron reagents. In this review, we described a series of bidentate ligands, such as bipyridine, 2-(pyridin-2-yl)-1H-indole, 2-(5-methyl-1H-pyrrol-2-yl)quinoline, N-(quinolin-8-yl)acetamide, 1,10-phenanthroline, and diketopyrrolopyrrole (DPP).

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“…introduced the concept that the formation of an ICT state and non‐radiative deactivation of that state competes with ISC to the excited triplet state, effectively decreasing the singlet oxygen yield [35] . Several other reports of this phenomenon for have followed; specifically in polar solvents, low 1 O 2 production is observed, as the ICT state is strongly stabilized and probability of reaching T 1 is low [36–39] …”

Section: Introductionmentioning

confidence: 99%

Highly Phototoxic Transplatin‐Modified Distyryl‐BODIPY Photosensitizers for Photodynamic Therapy

et al. 2020

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We report the synthesis of the first transplatin‐BODIPY conjugates for application in photodynamic therapy (PDT). The distyryl BODIPYs containing two iodine atoms were designed to absorb in the red region, easily undergo intersystem crossing for efficient singlet oxygen generation, and additionally offer the possibility for coordination with mono‐activated transplatin. We were able to demonstrate that coordination of the BODIPYs with a mono‐activated transplatin increases the phototoxic index of the photosensitizers significantly, giving rise to highly phototoxic distyryl BODIPY derivatives, of which one was shown to have the highest ever reported phototoxic index against any cell line. Furthermore, the photophysical mechanism of singlet oxygen generation in distyryl BODIPYs undergoing intramolecular charge transfer was studied experimentally and using time‐dependent density functional theory.

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Synthesis of a triphenylamine BODIPY photosensitizer with D–A configuration and its application in intracellular simulated photodynamic therapy

Abstract: A D–A type triphenylamine BODIPY fluorescent dye with AIE characteristics makes progress in photodynamic therapy.

Cited by 28 publications

References 48 publications

Photophysics of BODIPY Dyes: Recent Advances

Photophysics of BODIPY Dyes: Recent Advances

Recent Progress on Synthesis of N,N′-Chelate Organoboron Derivatives

Highly Phototoxic Transplatin‐Modified Distyryl‐BODIPY Photosensitizers for Photodynamic Therapy

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