corrole and phthalocyanine

The covalent and noncovalent association of self-assembling peptides and tetrapyrroles was explored as a way to generate systems that mimic Nature's functional supramolecular structures. Different types of peptides spontaneously assemble with porphyrins, phthalocyanines, or corroles to give long-range ordered architectures, whose structure is determined by the features of both components. The regular morphology and ordered molecular arrangement of these systems enhance the photochemical properties of embedded chromophores, allowing applications as photo-catalysts, antennas for dye-sensitized solar cells, biosensors, and agents for light-triggered therapies. Chemical modifications of peptide and tetrapyrrole structures and control over the assembly process can steer the organization and influence the properties of the resulting system. Here we provide a review of the field, focusing on the assemblies obtained from different classes of self-assembling peptides with tetrapyrroles, their morphologies and their applications as innovative functional materials.

Topics: Indoles; Isoindoles; Peptides; Photochemistry; Porphyrins; Tetrapyrroles

This review covers the synthesis of coumarin-porphyrin, coumarin-phthalocyanine and coumarin-corrole conjugates and their potential applications. While coumarin-phthalocyanine conjugates were obtained almost exclusively by tetramerization of coumarin-functionalized phthalonitriles, coumarin-porphyrin and coumarin-corrole conjugates were prepared by complementary approaches: (a) direct synthesis of the tetrapyrrolic macrocycle using formylcoumarins and pyrrole or (b) by functionalization of the tetrapyrrolic macrocycle. In the last approach a range of reaction types were used, namely 1,3-dipolar cycloadditions, hetero-Diels-Alder, Sonogashira, alkylation or acylation reactions. This is clearly a more versatile approach, leading to a larger diversity of conjugates and allowing the access to conjugates bearing one to up to 16 coumarin units.

Topics: Alkylation; Coumarins; Indoles; Isoindoles; Molecular Structure; Porphyrins; Pyrroles

A series of tris(pentafluorophenyl)corrole (TPFC) tin(IV) and tin(II) complexes were prepared and studied by various characterization techniques including (1)H, (19)F, and (119)Sn NMR and UV-vis spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. The unusual 4-coordinate, monomeric, divalent tin(II) complex [(TPFC)Sn(II)](-) (2a) showed highly efficient reactivity toward alkenes and alkyl halides via a nucleophilic addition pathway leading to the quantitative formation of alkyl stannyl corrole compounds. DFT calculations confirmed the divalent nature of the tin center in 2a, and an NBO analysis showed about 99.99% Sn lone pair character, of which 83.6% was Sn 5s and 16.35% was Sn 5p character.

Topics: Alkanes; Alkenes; Indicators and Reagents; Indoles; Isoindoles; Models, Molecular; Organotin Compounds; Porphyrins

Delivery strategies for porphyrinoid-based photosensitizers for use in therapeutic applications are based on a myriad of factors, which include porphyrinoid structure, solubility and cellular targets. These drug-delivery methods include encapsulation, hydrogels, protein carriers, nanoparticles and polymeric micelles among others. This article reviews the strategies for delivering porphyrinoids published to date and will focus on porphyrins, corroles, chlorins, bacteriochlorins, porphyrazines and phthalocyanines. Highlighted are the most recent and different strategies used for each of the corresponding porphyrinoid-based macrocycles.

Topics: Drug Delivery Systems; Indoles; Isoindoles; Micelles; Nanoparticles; Photosensitizing Agents; Porphyrins