Novel pyrene-BODIPY dyes based on cyclotriphosphazene scaffolds: Synthesis, photophysical and spectroelectrochemical properties

Çetindere, Seda; Tümay, Süreyya Oğuz; Şenocak, Ahmet; Kılıç, Adem; Durmuş, Mahmut; Demirbaş, E.; Yeşilot, Serkan

doi:10.1016/j.ica.2019.05.022

Cited by 34 publications

(27 citation statements)

References 50 publications

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“…Excitation (λ exc = 290 nm) of the Bn-OH-BDY dyad leads to emission (λ emi = 545 nm) directed by the BODIPY subunits pointing to excitation energy transfer (EET) from the ESIPT to BODIPY core. Two cyclotriphosphazene (Cpz) compounds bearing mono-and distyryl(pyrene) BODIPY dyes ( Figure 5) reported in 2019 [61]. These compounds indicated intense fluorescence emission even at very low concentrations.…”

Section: Photophysical Properties Of Bodipy Dyesmentioning

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: Photophysical Properties Of Bodipy Dyesmentioning

confidence: 99%

Photophysics of BODIPY Dyes: Recent Advances

Çetindere¹

2021

Photophysics, Photochemical and Substitution Reactions - Recent Advances

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“…The results received were matched with the expected structures as seen in the experimental part. In Figure 1, the molecular ion peak of the target compound was seen at m/z 548, additional peak which was seen at m/z 529 was attributed to the separation of fluorine, which is common in BODIPY compounds (33). The characteristic carbon-carbon triple bond and acetyl-CH stretch bands of the acetylene group were seen at 3292 and 2100 cm -1 on FT-IR spectra of EthyPy compound.…”

Section: Resultsmentioning

confidence: 96%

A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties

Alidağı

Çetindere

2021

Journal of the Turkish Chemical Society Section A: Chemistry

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In the present work, a novel highly conjugated pyrene-boron dipyrromethene (Py-BODIPY) 4 with a donor-acceptor (D-A) skeleton small molecule was synthesized by Sonogashira cross-coupling reaction between 1-ethynylpyrene (2) as a donor group and BODIPY 3 as an acceptor group. The new compound was characterized by fourier transform-infrared (FT-IR), nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MALDI-TOF) and elemental analysis. The photophysical and electrochemical properties of the compound 4 were investigated by UV-vis absorption, fluorescence emission spectroscopy, and cyclic voltammetry (CV) in dichloromethane. It was found from the optical and electroc hemical measurements that the target compound has highest occupied molecular orbital energy level (EHOMO) at-5.70 eV, lowest unoccupied molecular orbital energy level (ELUMO) at-3.27 eV, and the band gap was calculated as 2.43 eV. In addition, theoretical computational studies was also carried out via density functional theory (DFT) for investigation of molecular structure and energy levels of the compound. On the basis of these results, the novel Pyrene-BODIPY compound 4 could be potential candidate for organic light emitting diodes (OLEDs).

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“…Recently, there has been substantial interest in cyclophosphazenes because they not only have an extensive stability range but they can also ensure excellent photophysical properties in combination with suitable fluorescent dyes, such as BODIPYs [15][16][17][18][19] and pyrene derivatives [20][21][22]. Hexachlorocyclotriphosphazene is a versatile starting scaffold for the synthesis of new compounds, as the chlorine groups attached to the phosphorus atoms are easily substituted by various nucleophiles to form reactive cyclotriphosphazenes.…”

Section: Introductionmentioning

confidence: 99%

Pyrene-BODIPY-substituted novel water-soluble cyclotriphosphazenes: synthesis, characterization, and photophysical properties

Çetindere¹,

Yeşilot²,

Kılıç³

2020

Turk J Chem

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In the present work, pyrene-boron-dipyrromethene (BODIPY)-substituted novel water-soluble cyclotriphosphazene derivatives (6 and 7) were synthesized by click reactions between a cyclotriphosphazene derivative with a hydrophilic glycol side group (2) and BODIPYs (4 and 5). All of the new compounds (2, 6, and 7) were characterized by Fourier-transform infrared and nuclear magnetic resonance spectroscopy, as well as mass spectrometry and elemental analysis. The photophysical properties of the BODIPY-substituted cyclotriphosphazenes (6 and 7) were investigated by UV-Vis and fluorescence emission spectroscopy in water and water/solvent mixtures. It was found that the target compounds were soluble in water and could be potential candidates as water-soluble fluorescent dyes for the desired applications.

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Novel pyrene-BODIPY dyes based on cyclotriphosphazene scaffolds: Synthesis, photophysical and spectroelectrochemical properties

Cited by 34 publications

References 50 publications

Photophysics of BODIPY Dyes: Recent Advances

Photophysics of BODIPY Dyes: Recent Advances

A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties

Pyrene-BODIPY-substituted novel water-soluble cyclotriphosphazenes: synthesis, characterization, and photophysical properties

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