A phthalocyanine-porphyrin triad for ratiometric fluorescent detection of Lead(II) ions

Qi, Dongdong; Zhang, Jinghui; Zhang, Dongli; Zhu, Mengliang; Gong, Lei; Su, Chaorui; Lu, Wei; Bian, Yongzhong; Jiang, Jianzhuang

doi:10.1016/j.dyepig.2019.107941

Cited by 20 publications

(11 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ratiometric fluorescent response to metal cations can be realized by means of several photophysical mechanisms: intramolecular charge transfer (ICT) [ 14 , 15 ], resonance energy transfer (RET) between two chromophore fragments [ 16 , 17 , 18 ], excimer/exciplex formation [ 19 ], or excited state intramolecular proton transfer (ESIPT) [ 20 ]. Despite the obvious advantage, the number of ratiometric fluorescent probes for Hg 2+ cation is rather limited even for in vitro analysis, and most of them exploit Hg 2+ -induced spyrolactam ring opening of rhodamine dyes, which act as energy acceptor chromophores [ 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Ratiometric Detection of Mercury (II) Ions in Living Cells Using Fluorescent Probe Based on Bis(styryl) Dye and Azadithia-15-Crown-5 Ether Receptor

Panchenko

Efremenko

Feofanov

et al. 2021

Sensors

View full text Add to dashboard Cite

Bis(styryl) dye 1 bearing N-phenylazadithia-15-crown-5 ether receptor has been evaluated as a ratiometric fluorescent chemosensor for mercury (II) ions in living cells. In aqueous solution, probe 1 selectively responds to the presence of Hg2+ via the changes in the emission intensity as well as in the emission band shape, which is a result of formation of the complex with 1:1 metal to ligand ratio (dissociation constant 0.56 ± 0.15 µM). The sensing mechanism is based on the interplay between the RET (resonance energy transfer) and ICT (intramolecular charge transfer) interactions occurring upon the UV/Vis (380 or 405 nm) photoexcitation of both styryl chromophores in probe 1. Bio-imaging studies revealed that the yellow (500–600 nm) to red (600–730 nm) fluorescence intensity ratio decreased from 4.4 ± 0.2 to 1.43 ± 0.10 when cells were exposed to increasing concentration of mercury (II) ions enabling ratiometric quantification of intracellular Hg2+ concentration in the 37 nM–1 μM range.

show abstract

Section: Introductionmentioning

confidence: 99%

Ratiometric Detection of Mercury (II) Ions in Living Cells Using Fluorescent Probe Based on Bis(styryl) Dye and Azadithia-15-Crown-5 Ether Receptor

Panchenko

Efremenko

Feofanov

et al. 2021

Sensors

View full text Add to dashboard Cite

show abstract

“… Schematic of phthalocyanine−porphyrin heterodyads for the detection of Pb 2+ ion by fluorescence resonance energy transfer (FRET). Reproduced from ref [ 38 , 40 , 41 ]. …”

Section: Figurementioning

confidence: 99%

“…The LOD for detecting Pb 2+ can be decreased to sub-parts per billion. Qi et al [41] have used the same principle to design the phthalocyanine-porphyrin hetero-triad H 2 Pc-β-(ZnPor) 2 (16) for Pb 2+ ions detection. Li et al [38] have synthesized a naphthalimide-porphyrin hybrid (17) (Figure 6) for the ratiometric detection of Hg 2+ in an aqueous solution and living cells.…”

Section: Detecting Mechanism Of Fluorescent Porphyrin Molecular Probesmentioning

confidence: 99%

Recent Advances in Porphyrin-Based Materials for Metal Ions Detection

Cheng

et al. 2020

IJMS

View full text Add to dashboard Cite

Porphyrins have planar and conjugated structures, good optical properties, and other special functional properties. Owing to these excellent properties, in recent years, porphyrins and their analogues have emerged as a multifunctional platform for chemical sensors. The rich chemistry of these molecules offers many possibilities for metal ions detection. This review mainly discusses two types of molecular porphyrin and porphyrin composite sensors for metal ions detection, because porphyrins can be functionalized to improve their functional properties, which can introduce more chemical and functional sites. According to the different application materials, the section of porphyrin composite sensors is divided into five sub-categories: (1) porphyrin film, (2) porphyrin metal complex, (3) metal–organic frameworks, (4) graphene materials, and (5) other materials, respectively.

show abstract

“…Phthalocyanine-porphyrin (Pc-Por) hetero-array systems owing to their unique composition show specific intramolecular interactions, [1][2][3][4][5][6][7][8][9][10][11][12] which result in efficient photo-induced electron and/or energy transfer processes from porphyrin to phthalocyanine macrocycle and typically strong fluorescence of the latter due to fluorescence resonance energy transfer (FRET) process. [11,12] This renders them good candidates for application in electrochemical catalysis, [13] light-harvesting [14,15] and optoelectronic devices. [16] By themselves, phthalocyanines and porphyrins, in particular, chlorin e 6 derivatives, are also known as quite efficient photosensitizers (PSs) used in photodynamic therapy (PDT) owing to the ability of the photo-induced singlet oxygen ( 1 O 2 ) generation.…”

Section: Introductionmentioning

confidence: 99%

A Covalently Linked Dyad Based on Zinc Phthalocyanine and Methylpheophorbide a: Synthetic and Physicochemical Study

Balashova¹,

Tolbin²,

Tarakanov³

et al. 2021

MHC

View full text Add to dashboard Cite

The first covalently linked conjugate of metal phthalocyaninate and chlorin e 6 derivative has been obtained by transesterification of α-ketomethyl ester in methylpheophorbide a with zinc(II) 2-(2-hydroxymethylbenzyloxy)-9(10),16(17),23(24)-tri-tert-butylphthalocyaninate under mild conditions. The dyad exhibits a panchromatic nature revealing both the phthalocyanine and pheophorbide derived bands in the UV-Vis absorption spectrum. The 1 H NMR spectroscopy data combined with theoretical calculations indicate the presence of spatial intramolecular interactions between the phthalocyanine, pheophorbide and spacer fragments of the dyad allowing to forecast its enhanced nonlinear optical properties, as well as the characteristic energy transfer from the excited pheophorbide subunit to the phthalocyanine core. Indeed, when excited in the UV-Vis range, the conjugate shows red fluorescence with the spectral maximum at 686 nm, which is close to the one of the initial zinc phthalocyaninate. Furthermore, the dyad effectively generates singlet oxygen and, in the presence of polyvinylpyrrolidone (PVP) as biocompatible solubilizer, forms stable micellar saline solutions with the particles ranged in size between 40 and 100 nm. These nanoparticles represent promising third-generation photosensitizing systems for application in theranostics.

show abstract

A phthalocyanine-porphyrin triad for ratiometric fluorescent detection of Lead(II) ions

Cited by 20 publications

References 32 publications

Ratiometric Detection of Mercury (II) Ions in Living Cells Using Fluorescent Probe Based on Bis(styryl) Dye and Azadithia-15-Crown-5 Ether Receptor

Ratiometric Detection of Mercury (II) Ions in Living Cells Using Fluorescent Probe Based on Bis(styryl) Dye and Azadithia-15-Crown-5 Ether Receptor

Recent Advances in Porphyrin-Based Materials for Metal Ions Detection

A Covalently Linked Dyad Based on Zinc Phthalocyanine and Methylpheophorbide a: Synthetic and Physicochemical Study

Contact Info

Product

Resources

About