Synthesis of NIR fluorescent thienyl-containing aza-BODIPY and its application for detection of Hg2+: Electron transfer by bonding with Hg2+

Jiang, Xin‐Dong; Zhao, Jiuli; Li, Qian; Sun, Chang‐Liang; Guan, Jian; Sun, Gao-Tao; Xiao, Lin-Jiu

doi:10.1016/j.dyepig.2015.09.023

Cited by 57 publications

(24 citation statements)

References 53 publications

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“…Owing to their advantageous and tunable photophysical properties and ability to generate singlet oxygen ( 1 O 2 )c oupled with absorption of light from the socalled "therapeuticw indow"( 600 nm-1100 nm), aza-BODIPY dyes have been proposed as potential triplet photosensitizers for both anti-microbiala nd anti-cancer photodynamic therapy. [20,[30][31][32][33][34][35][36][37][38][39][40][41] Aza-BODIPYs continue to attracta ttention as chemosensors for the detection of ammonia, [42] cysteine, homocysteine and glutathione in living cells, [43] Hg 2 + , [44][45][46] F À , [47,48] in vivo detection of H 2 S, [49] carbon dioxide, [50] glucosei nw hole blood, [51] detection of saxitoxin [52] and pH-sensitive sensors. [52] Furthermore, aza-BODIPYs have been proposed as photoactive components in photovoltaic devices [54][55][56] and nonlinear optical materials.…”

Section: Introductionmentioning

confidence: 99%

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Gut

Łapok

Drelinkiewicz

et al. 2017

Chemistry An Asian Journal

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As eries of novel iodinated NO 2 -substituted azaBODIPYs have been synthesized and characterized.H ighly desirable photophysical and photochemical properties were induced in NO 2 -substituted aza-BODIPYs by iodinationo ft he pyrrole rings. In particular, highv alues of singlet oxygen quantum yields (F D )r anging from 0.79 to 0.85 were measured. The photooxygenation process proceeds via aT ype II mechanism under the experimental conditions applied. The compounds studied exhibited an absorption band within the so-called "therapeutic window", with l max located between 645 nm to 672 nm. They were non-fluorescent at room temperature with excited singlet-state lifetimes within the picosecond range as measured by femtosecond transient absorption. Nanosecond laser flash photolysis experiments revealed T 1 !T n absorption spanning from ca. 400 nm to ca. 500 nm and allowedd etermination of the triplet-state lifetimes. The estimated triplet lifetimes (t T )i nd eaerated acetonitrile ranged between 2.74 msa nd 3.50 ms. As estimated by CV/DPV measurements, all iodinateda za-BODIPYs studied exhibited one irreversible oxidation and two quasireversible reductions processes. Estimation of the E HOMO gave the value of À6.06 to À6.26 eV while the E LUMO was found to be located at ca. À4.6 eV.T hermogravimetric (TGA) analysis revealed that iodinated aza-BODIPYs weres table up to approximately 300 8C. All compounds studied exhibit high photostability in toluene solution.

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Section: Introductionmentioning

confidence: 99%

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Gut

Łapok

Drelinkiewicz

et al. 2017

Chemistry An Asian Journal

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“…We found that the dipyrroles successfully led to the synthesis of aestheticallys ymmetrical aza-BODIPY dyes 3 and 4 on treatment with AcOH, Ac 2 O, and NaNO 2 ,f ollowed by complexation with Et 3 NÀBF 3 ·Et 2 O( Scheme 1). [5,10] The structures of these compounds were unambiguously confirmed by detailed characterization, including NMR spectroscopy and HRMS (ESI) analyses (see the Supporting Information). To the best of our knowledge,t hesea za-BODIPY structures are the first to bear 1methyl-1 H-pyrrolyl groups at the 3,5-positions.…”

Section: Resultsmentioning

confidence: 82%

“…[10] Furthermore, bipyrrole 6 was also successfully obtained by using 3-acetyl-1-methylpyrrole as the starting material.P yrrole 5 showedadiagnostic signal at d = 8.12 ppm (br s, 1H;N ÀH) in its 1 HNMR spectrum( See the SupportingI nformation), in agreement with that of the reported compound 1 in the pyrrole family at d = 8.34 ppm (br s, 1H;N ÀH). [5,10] Moreover,p yrrole 5 also showed ad istinct high-field 1 HNMR signal for the methyl group at d = 3.68 ppm (s, 1H;N ÀCH 3 ). Similarly,p yrrole 6 exhibited typical 1 HNMR signals.…”

Section: Resultsmentioning

confidence: 96%

“…[4] Moreover,freezing the rotationo ft he aryl substituentsa tt he 3,5-positions caused the aza-BODIPY dyes to show fluorescence maximaa t7 00-900 nm and narrow excitation/emission bands. [5] In addition, NIR-fluorescent aza-BODIPY dyest hat contained naphthyl groups at the 3,5-positions could also be ap otentialp hotosensitizer (PS) fors inglet-oxygeng eneration. [6] Therefore, such aza-BODIPY derivativesa re widely considered to be good candidates for biological labeling applicationsa nd fluorescent materials.…”

Section: Introductionmentioning

confidence: 99%

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New Near‐Infrared‐Fluorescent Aza‐BODIPY Dyes with 1‐Methyl‐1 H‐Pyrrolyl Substituents at the 3,5‐Positions

Jiang

Guan

et al. 2016

Asian J Org Chem

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New near-infrared-fluorescent aza-BODIPY dyes with 1-methyl-1 H-pyrrolyls ubstituents at the 3,5-positions were successfully prepared and the 1-methyl-1 H-pyrrolyl groups had an oticeable effect on their photophysicalp roperties. The absorption and emission maximao fa za-BODIPY dye 4 (l abs = 754 nm, l em = 803 nm) that contained 1-methyl-1 H-pyrrolyl groups were bathochromically shifted compared to those of typical aza-BODIPY dye 1 (l abs = 649 nm, l em = 673 nm), which contained phenylg roups. The photophysical data were well-supported and explainedb yM Oc alculations. Aza-BODIPY dye 3 was stable and suited for labeling living cells for imaging assays in the near-infrared region.

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“…Recently, our interest has been in design and synthesis of azaBODIPY‐based dyes as near‐infrared (NIR) fluorescent probes . AzaBODIPY dyes are known to be highly fluorescent, stable, and exceptionally insensitive to the polarity of solvents, and are widely applied as fluorophores in probes or sensors .…”

Section: Introductionmentioning

confidence: 99%

NIR Fluorescent AzaBODIPY‐Based Probe for the Specific Detection of L–Lysine

et al. 2018

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With 1‐(5‐chloro‐thiophen‐2‐yl)‐ethanone as the starting material, 3,5‐dichloro‐azaBODIPY 2 was successfully prepared. AzaBODIPY can be modified by nucleophilic monosubstitution with N‐nucleophile at room temperature. Since the previous work on specifically detecting L‐lysine (Lys) is scarce, dichloro‐azaBODIPY 2 is valuable as a probe for detecting Lys. Probe 2 was found to be selective and sensitive to Lys. Moreover, probe 2 can be used to detect Lys in PC3 cells, indicating its potential application for studying the effect of Lys in biological systems.

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Synthesis of NIR fluorescent thienyl-containing aza-BODIPY and its application for detection of Hg2+: Electron transfer by bonding with Hg2+

Cited by 57 publications

References 53 publications

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

New Near‐Infrared‐Fluorescent Aza‐BODIPY Dyes with 1‐Methyl‐1 H‐Pyrrolyl Substituents at the 3,5‐Positions

NIR Fluorescent AzaBODIPY‐Based Probe for the Specific Detection of L–Lysine

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