Carbazole substituted BODIPY dyes: Synthesis, photophysical properties and antitumor activity

Sengul, İbrahim F.; Okutan, Elif; Kandemir, Hakan; Astarcı, Erhan; Çoşut, Bünyemin

doi:10.1016/j.dyepig.2015.07.025

Cited by 33 publications

(6 citation statements)

References 32 publications

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“…It is noteworthy that the MALDI-TOF MS analyses of BDY-3T-BDY and BDY-4T-BDY exhibited up to four different peak groups corresponding to the protonated molecular ions ([M + H] + ) and ions formed by rupture of fluorine atom(s) and/or methyl groups ([M – F] + , [M – 4×CH 3 – F] + , [M – 4×CH 3 – 2F] + ) (Figures S3 and S4). On the basis of conventional melting temperature measurements and differential scanning calorimetry (DSC) analysis, no thermal transitions were observed until decomposition. However, thermogravimetric (TGA) analysis indicates reasonable thermal stability of the new molecules with decomposition thresholds located at ∼325 °C (Figure S5).…”

Section: Resultsmentioning

confidence: 99%

Solution-Processable BODIPY-Based Small Molecules for Semiconducting Microfibers in Organic Thin-Film Transistors

Özdemir

Choi

Kwon

et al. 2016

ACS Appl. Mater. Interfaces

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Electron-deficient π-conjugated small molecules can function as electron-transporting semiconductors in various optoelectronic applications. Despite their unique structural, optical, and electronic properties, the development of BODIPY-based organic semiconductors has lagged behind that of other π-deficient units. Here, we report the design and synthesis of two novel solution-proccessable BODIPY-based small molecules (BDY-3T-BDY and BDY-4T-BDY) for organic thin-film transistors (OTFTs). The new semiconductors were fully characterized by (1)H/(13)C NMR, mass spectrometry, cyclic voltammetry, UV-vis spectroscopy, photoluminescence, differential scanning calorimetry, and thermogravimetric analysis. The single-crystal X-ray diffraction (XRD) characterization of a key intermediate reveals crucial structural properties. Solution-sheared top-contact/bottom-gate OTFTs exhibited electron mobilities up to 0.01 cm(2)/V·s and current on/off ratios of >10(8). Film microstructural and morphological characterizations indicate the formation of relatively long (∼0.1 mm) and micrometer-sized (1-2 μm) crystalline fibers for BDY-4T-BDY-based films along the shearing direction. Fiber-alignment-induced charge-transport anisotropy (μ∥/μ⊥ ≈ 10) was observed, and higher mobilities were achieved when the microfibers were aligned along the conduction channel, which allows for efficient long-range charge-transport between source and drain electrodes. These OTFT performances are the highest reported to date for a BODIPY-based molecular semiconductor, and demonstrate that BODIPY is a promising building block for enabling solution-processed, electron-transporting semiconductor films.

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Section: Resultsmentioning

confidence: 99%

Solution-Processable BODIPY-Based Small Molecules for Semiconducting Microfibers in Organic Thin-Film Transistors

Özdemir

Choi

Kwon

et al. 2016

ACS Appl. Mater. Interfaces

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“…The BODIPYs 107 and 108 exhibited strong absorption around 503 nm and fluorescence at 512 nm; cytotoxicity assays in HT29 cancer cells revealed that, 108 is more toxic than 107 (Chart 15). The observed IC 50 values for 107 and 108 were 21.7 ng/mL and 8.3 ng/mL, respectively (Sengul et al, 2015).…”

Section: Carbazole Bridged Bodipy Dimersmentioning

confidence: 95%

“…3.1% by a hole mobility mechanism (Liao et al, 2017a). Also, compound 105 (Chart 14) showed decent cytotoxic activity against HT29 cell lines (Sengul et al, 2015). In another report Gupta et al synthesized N-butylcarbazole bridged BODIPY dimer 106 (Chart 14); the compound showed bathochromic shift in the emission band with good Stokes shift of 83 nm (Kesavan et al, 2015).…”

Section: Carbazole Bridged Bodipy Dimersmentioning

confidence: 99%

“…Meso-carbazole substituted BODIPY 107 and N-alkylcarbazole bridged BODIPY dimer 108 (Chart 15) were prepared and their biological activities were tested in the human colon cancer cell lines (Sengul et al, 2015). The BODIPYs 107 and 108 exhibited strong absorption around 503 nm and fluorescence at 512 nm; cytotoxicity assays in HT29 cancer cells revealed that, 108 is more toxic than 107 (Chart 15).…”

Section: Carbazole Bridged Bodipy Dimersmentioning

confidence: 99%

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Carbazole Substituted BODIPYs

Gupta¹,

Kesavan²

2019

Front. Chem.

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Difluoroboron-dipyrromethenes (BODIPYs) are highly popular fluorescent dyes with applications as NIR probes for bioimaging, fluorescent tags/sensors and as photosensitizers in cancer therapy and organic photovoltaics. This review concentrates on the synthesis and spectral properties of BODIPY dyes conjugated with carbazole heterocycle. The carbazole is an electron rich tricyclic compound and due to its excellent electronic properties, it is extensively used in the production of electroluminescent materials and polymers. This review highlights the recent progress made on the series of BODIPY derivatives containing carbazole ring at alpha, beta, and meso-positions of the BODIPY skeleton. Carbazole based hybrid BODIPYs, carbazole linked aza-BODIPYs and carbazole-fused BODIPYs are also discussed.

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“…Over the last few decades, BODIPY has been well‐known group of highly fluorescent dyes . It is worthwhile to design and synthesize new BODIPY platforms as they represent outstanding photophysical properties such as high fluorescence quantum yield, large extinction coefficient, and high chemical, thermal and photophysical stability . The BODIPY skeleton is a key structural component in many applications, including light harvesting materials, optical chemosensors, fluorescent biolabeling reagents and photodynamic therapy reagents .…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Sensing of Cesium Ions by an Amide‐Linked BODIPY Dye: Synthesis and Photophysical Properties

Özcan

Çoşut

2018

ChemistrySelect

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In this study, a new fluorescent sensor for Cs + ion was designed and synthesized from the combination of pyridine-2,6-dicarboxamide and 4,4-difluoro-4-borata-3a,4a-diaza-s-indacene (BODI-PY) scaffolds. The sensing capability of the target compound against a variety of ions was investigated. The structure of the target compound was proved by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and 1 H and 13 C NMR spectroscopies. Photophysical properties of the amidelinked BODIPY compound were studied by utilizing fluorescence spectroscopies in DMSO/water (9:1, v/v) solution. It was found that the final amide-linked BODIPY compound showed exclusively selective and sensitive turn-off sensor behavior for Cs + ion over other metal ions (+ ). The addition of Cs + resulted in quenching of fluorescence intensity and the detection limit was calculated to be 0.273 mM. According to Job's Plot, binding stoichiometry ratio of the target compound with Cs + was 1:1.

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Carbazole substituted BODIPY dyes: Synthesis, photophysical properties and antitumor activity

Cited by 33 publications

References 32 publications

Solution-Processable BODIPY-Based Small Molecules for Semiconducting Microfibers in Organic Thin-Film Transistors

Solution-Processable BODIPY-Based Small Molecules for Semiconducting Microfibers in Organic Thin-Film Transistors

Carbazole Substituted BODIPYs

Fluorescent Sensing of Cesium Ions by an Amide‐Linked BODIPY Dye: Synthesis and Photophysical Properties

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