Efficient energy transfer in phenyl-ethynyl-linked asymmetric BODIPY dimers

Hewavitharanage, Priyadarshine; Warshawsky, Reuben; Rosokha, Sergiy V.; Vaal, Jason; Stickler, Kelsey; Bachynsky, Dmitriy; Jairath, Neil

doi:10.1016/j.tet.2020.131515

Cited by 4 publications

(11 citation statements)

References 56 publications

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“…The UV-Vis absorption and fluorescence experiments were carried out in THF using a Cary 5000 Series UV-VIS-NIR Spectrophotometer. Similar to our previous photophysical data in CH2Cl2 [39], compounds 1 and 2 show typical BODIPY absorption bands (Figure 3), the more prominent, lowest energy absorption band due to the S0-S1 (π-π*) transition and the weaker absorption band, ~350-430 nm which is more prominent in compound 2, is due to the S0-S2 (π-π*) transition (Figure 3) [1,39]. Absorption maximum of the BODIPY 2 which has ethynylthiophene units at the 2,6 positions is a 65 nm redshifted in comparison to compound 1 (Table 1).…”

Section: Photophysical Propertiessupporting

confidence: 88%

“…Fluorescence energy transfer can occur through bond or through space. When the donor and the acceptor are linked through a twisted conjugated spacer, through bond energy transfer predominates [1][2][3]. Through-space energy transfer known as fluorescence resonance energy transfer (FRET) or Förster energy transfer occurs through long-range dipoledipole interactions between the donor-acceptor pair [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

“…BODIPY has been extensively studied for many applications such as labeling of biomolecules, imaging, laser dyes, solar cells, chemical sensors, fluorescent indicators and probes, and ion sensors [25,26]. BODIPY based donor/ acceptor systems such as energy transfer cassettes and artificial light harvesting arrays are also reported [1,27,28]. Most of the organic dyes (including BODIPY) are hydrophobic in nature.…”

Section: Introductionmentioning

confidence: 99%

“…In a previous study, we reported highly efficient energy transfer in an asymmetric dimeric BODIPY [1]. Arrangement of the BODIPY units in the dimers were investigated by DFT calculations.…”

Section: Introductionmentioning

confidence: 99%

“…Arrangement of the BODIPY units in the dimers were investigated by DFT calculations. Perpendicular arrangement of BODIPY core breaks the conjugation between two BODIPY units which enables donor-acceptor behavior with efficient excitation energy transfer [1]. However, the synthesis and purification of these dimers are highly time consuming and often gives a poor yield.…”

Section: Introductionmentioning

confidence: 99%

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Highly efficient fluorescence resonance energy transfer in co-encapsulated BODIPY nanoparticles

2021

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Fluorescence resonance energy transfer (FRET) is a powerful tool used in a wide range of applications due to its high sensitivity and many other advantages. Co-encapsulation of a donor and an acceptor in nanoparticles is a useful strategy to bring the donor-acceptor pair in proximity for FRET. A highly efficient FRET system based on BODIPY-BODIPY (BODIPY: boron-dipyrromethene) donor-acceptor pair in nanoparticles was synthesized. Nanoparticles were formed by co-encapsulating a green emitting BODIPY derivative (FRET donor, lmax = 501 nm) and a red emitting BODIPY derivative (FRET acceptor, lmax = 601 nm) in an amphiphilic polymer using the precipitation method. Fluorescence measurements of encapsulated BODIPY in water following 501 nm excitation caused a 3.6 fold enhancement of the acceptor BODIPY emission at 601 nm indicating efficient energy transfer between the green emitting donor BODIPY and the red emitting BODIPY acceptor with a 100 nm Stokes shift. The calculated FRET efficiency was 96.5%. Encapsulated BODIPY derivatives were highly stable under our experimental conditions.

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Section: Photophysical Propertiessupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…In a previous study, we reported highly efficient energy transfer in an asymmetric dimeric BODIPY [1]. Arrangement of the BODIPY units in the dimers were investigated by DFT calculations.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Highly efficient fluorescence resonance energy transfer in co-encapsulated BODIPY nanoparticles

2021

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Substituent Effects in Six(Anilido)‐Five(Thiazole) Membered Ring Boron Difluoride Dyes

et al. 2021

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A series of new six (anilido)-five (thiazole) membered ring boron difluoride dyes, namely BFs, have been synthesized from the corresponding para-and meta-substituted 2-(2'-methylaminophenyl) benzothiazoles through complexation with boron trifluoride. Depending on the substituent effect, the derivatives can switch the emission properties from fluorescence with 100 % emission yield to slim fluorescence but > 90 % triplet state population and peak wavelength tuning from 490 nm to 610 nm. Compared with non-complexed precursors, the rigid, highly planar structure and significantly red-shifted absorption and emission for BFs indicate that the boron center facilitates the formation of a bridge leading to increased rigidity, and is also involved in π-conjugation, increasing the transition dipole and suppressing the nonradiative internal conversion. Together with optical ~100 % transparent window around 325-375 nm, BFs may find unique applications, among which the fluorescence up-conversion via triplet-triplet annihilation is demonstrated.

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Engineering a “dual-key-and-lock” ratiometric fluorescent nanoprobe for real-time reporting the freshness and quality of meat

Xiao

Shen²,

Cao³

et al. 2023

Food Chemistry

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Efficient energy transfer in phenyl-ethynyl-linked asymmetric BODIPY dimers

Cited by 4 publications

References 56 publications

Highly efficient fluorescence resonance energy transfer in co-encapsulated BODIPY nanoparticles

Highly efficient fluorescence resonance energy transfer in co-encapsulated BODIPY nanoparticles

Substituent Effects in Six(Anilido)‐Five(Thiazole) Membered Ring Boron Difluoride Dyes

Engineering a “dual-key-and-lock” ratiometric fluorescent nanoprobe for real-time reporting the freshness and quality of meat

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