4-4-difluoro-4-bora-3a-4a-diaza-s-indacene and phthalocyanine

The present work describes the first synthesis of novel asymmetric zinc (II) phthalocyanine (ZnPc) including three boron dipyrromethene (BODIPY) and one ethyloxy azido moieties. Moreover, single walled carbon nanotube (SWCNT) surface was functionalized by this ZnPc containing BODIPY; using the azide-alkyne Huisgen cycloaddition (Click) reaction to obtain SWCNT-ZnPc hybrid material. Structural, thermal and morphological characterizations of both ZnPc and SWCNT-ZnPc hybrid were carried out in-depth by spectroscopic, thermal and microscopic techniques. In this study, the synthesized SWCNT-ZnPc material was decorated on composite glassy carbon electrode (GCE) by means of an easy and a practical drop cast method. The modified electrode was tested as a non-enzymatic electrochemical sensor in various common pesticides such as methyl parathion, deltamethrin, chlorpyrifos and spinosad. Electrochemical behavior of non-enzymatic electrode (GCE/SWCNT-ZnPc) was determined via cyclic voltammetry and differential pulse voltammetry. The non-enzymatic sensor demonstrated high selectivity for methyl parathion in a wide linear range (2.45 nM-4.0 × 10

Topics: Boron Compounds; Citrus sinensis; Electrochemical Techniques; Fruit and Vegetable Juices; Indoles; Isoindoles; Molecular Structure; Nanotubes, Carbon; Pesticide Residues; Pesticides; Prunus persica

This work reports on the synthesis of nanoassemblies of supramolecular hybrids containing detonated nanodiamonds (DNDs) covalently linked to halogenated BODIPY (DNDs-BODIPY) by an amide bond, followed by π-π stacking of 2,9,16,23-tetrakis[4-(N-methylpyridyloxy)]-phthalocyanine (ZnTPPcQ) on the DNDs-BODIPY conjugate, to form nanoassembly represented as ZnTPPcQ-DNDs-BODIPY. ZnTPPcQ-DNDs-BODIPY has a higher singlet oxygen quantum yield of 0.50 in water. Therefore, the construction of a three component photodynamic therapy agent (ZnTPPcQ-DNDs-BODIPY) as a single photosentisiser improved singlet quantum yields of the Pc. Zeta potential studies of ZnTPPcQ-DNDs-BODIPY under various temperatures, concentrations and pH conditions, showed the conjugate is more stable at pHs 2, 4 and 7 and at high concentrations (50 μg/mL) and temperatures (80 °C). ZnTPPcQ-DNDs-BODIPY showed high photodynamic therapy (PDT) activity with a low MCF-7 cell viability of 21 ± 5% when compared to 31 ± 2%, 30 ± 2% and 28 ± 2% cell viability at the highest tested concentration of 50 μg/mL for DNDs, ZnTPPcQ-DND and DNDs-BODIPY, respectively.

Topics: Boron Compounds; Cell Line, Tumor; Cell Survival; Fluorescent Dyes; Humans; Hydrogen-Ion Concentration; In Vitro Techniques; Indoles; Isoindoles; Nanodiamonds; Photochemotherapy; Photosensitizing Agents; Singlet Oxygen

Topics: Animals; Boron Compounds; Fluorescent Dyes; Indoles; Isoindoles; Melanoma; Mice; Molecular Structure; Pyrenes; Tumor Cells, Cultured

Topics: Antigens, Neoplasm; Biomarkers, Tumor; Biosensing Techniques; Boron Compounds; Electrodes; Equipment Design; Fluorescent Dyes; Humans; Indoles; Isoindoles; Keratin-19; Limit of Detection; Lung Neoplasms; Magnesium Oxide; Paper; Stochastic Processes

A novel type of phthalocyanine pentad containing four boron dipyrromethene (BODIPY) units at peripheral positions of the phthalocyanine framework has been designed and synthesized for the first time. The Sonogashira coupling reaction between 4,4'-difluoro-8-(4-ethynyl)-phenyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (Ethynyl-BODIPY) and 2(3),9(10),16(17),23(24)-tetrakis(iodo) zinc(ii) phthalocyanine (Iodo-Pc) has been used for the synthesis of the target compound. The BODIPY-phthalocyanine pentad dye (BODIPY-Pc) has been fully characterized by (1)H NMR, MALDI-TOF mass, FT-IR and UV-Vis spectroscopic techniques and elemental analysis as well. The photoinduced energy transfer process for this dye system was explored in tetrahydrofuran solution. The singlet oxygen generation capability and photodegradation behaviours of this BODIPY-Pc pentad dye were also investigated in DMSO for the determination of the usability of this new type of dye system as a photosensitizer in PDT applications.

Topics: Boron Compounds; Chemistry Techniques, Synthetic; Coloring Agents; Drug Design; Energy Transfer; Indoles; Isoindoles; Photolysis; Photosensitizing Agents; Singlet Oxygen

A panchromatic 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-zinc phthalocyanine conjugate (Bodipy-ZnPc) 1 was synthesized starting from phthalocyanine aldehyde 4, via dipyrromethane 3 and dipyrromethene 2. Conjugate 1 represents the first example in which a Bodipy unit is tethered to the peripheral position of a phthalocyanine core. Electrochemical and optical measurements provided evidence for strong electronic interactions between the Bodipy and ZnPc constituents in the ground state of 1. When conjugate 1 is subjected to photoexcitation in the spectral region corresponding to the Bodipy absorption, the strong fluorescence characteristic of the latter subunit is effectively quenched (i.e., > or = 97%). Excitation spectral analysis confirmed that the photoexcited Bodipy and the tethered ZnPc subunits interact and that intraconjugate singlet energy transfer occurs with an efficiency of ca. 25%. Treatment of conjugate 1 with N-pyridylfulleropyrrolidine (8), an electron-acceptor system containing a nitrogen ligand, gives rise to the novel electron donor-acceptor hybrid 1<-->8 through ligation to the ZnPc center. Irradiation of the resulting supramolecular ensemble within the visible range leads to a charge-separated Bodipy-ZnPc(*+)-C(60)(*-) radical-ion-pair state, through a sequence of excited-state and charge transfers, characterized by a remarkably long lifetime of 39.9 ns in toluene.

Topics: Boron Compounds; Dimerization; Electrochemistry; Fluorescence; Fullerenes; Indoles; Isoindoles; Models, Chemical; Organometallic Compounds; Photochemistry; Porphobilinogen; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Zinc Compounds

Two novel silicon(IV) phthalocyanines substituted axially with two BODIPY or mono-styryl BODIPY moieties have been synthesised, which exhibit predominantly a photo-induced energy or electron-transfer process in toluene depending on the axial substituents.

Topics: Boron Compounds; Electrons; Fluorescent Dyes; Indoles; Isoindoles; Molecular Structure; Photochemistry; Radiation-Sensitizing Agents; Silicon; Toluene

Two novel subphthalocyanines substituted axially with a BODIPY or distyryl BODIPY moiety have been synthesized. Both systems exhibit a highly efficient photoinduced energy transfer process, either from the excited BODIPY to the subphthalocyanine core (for the former) or from the excited subphthalocyanine to the distyryl BODIPY unit (for the latter).

Topics: Boron Compounds; Energy Transfer; Indoles; Isoindoles; Spectrometry, Fluorescence