Hokkaido University · Materials Science
Professor Yasuhide Inokuma's research lab specializes in the synthesis and functionalization of subporphyrins—ring-contracted porphyrin congeners with unique bowl-shaped architectures and distinct electronic properties. The lab focuses on developing novel synthetic methodologies for meso-substituted subporphyrins, including one-pot condensations and transition-metal-catalyzed reactions, to access structurally diverse and highly tunable macrocycles. Key research directions include tuning optical and electronic properties through axial ligand exchange, meso-substituent engineering, and the design of stimuli-responsive systems such as cation sensors and two-photon absorbing materials. The lab also explores the fundamental aromaticity and excited-state behavior of these systems, particularly in relation to their fluorescence and nonlinear optical properties.
Figures are computed from collected data and may differ slightly.
Keeping it in the family: A one-pot condensation with a boric acid template leads to the synthesis of subporphineboron(III) complexes (see example; B green, O red, N blue, C turquoise, H white), ring-contracted congeners of porphyrins. Facile axial ligand exchange reactions provide alkoxy- and carboxy-coordinated subporphyrins, which have bowl-shaped structures with a bowl depth that depends on the axial group. Supporting information for this article is available on the WWW under http://www.wile
Two synthetic methods of meso-aryl-substituted subporphyrins have been developed by means of the reaction of pyridine-tri-N-pyrrolylborane with a series of aryl aldehydes. One method relies on the condensation under Adler conditions with chloroacetic acid in refluxing 1,2-dichlorobenzene to afford subporphyrins in 1.1-3.2%, and the other is a two-step reaction consisting of the initial treatment of the two substrates with trifluoroacetic acid at 0 degrees C followed by air-oxidation in refluxing
Subporphyrin is a ring-contracted porphyrin congener consisting of three pyrrolic subunits domed in a C3 symmetric bowl arrangement. Subporphyrin had long been elusive until the first synthesis of tribenzosubporphine in 2006. Shortly after, synthetic protocols of subpyriporphyrin, meso-aryl-substituted subporphyrins, and meso-aryl substituted subchlorins were developed. Subporphyrins display interesting properties including distinct aromaticity arising from 14pi-electronic conjugation, green flu
Es bleibt in der Familie: Eine Eintopfkondensation mit einem Borsäuretemplat ermöglicht die Synthese von Subporphinbor(III)-Komplexen (siehe Beispiel; B grün, O rot, N blau, C türkis, H weiß), ringverengten Artverwandten der Porphyrine. Der einfache Austausch axialer Liganden liefert alkoxy- und carboxykoordinierte Subporphyrine mit schalenförmigen Strukturen, wobei die Schalentiefe von der axialen Gruppe abhängt.
Go with the glow: A series of meso-oligo(1,4-phenyleneethynylene) substituted subporphyrins shows a significant amplification in absorption coefficient and fluorescence quantum yield as the chain length of the substituents increases (see picture). Particularly, enhancement of the two-photon absorption properties along the series can be characterized by an octupolar effect rather than a conjugation effect. Supporting information for this article is available on the WWW under http://www.wiley-vch.
A series of meso-(4-(N,N-dibenzylamino)phenyl)-substituted subporphyrins was synthesized by means of Buchwald-Hartwig amination protocol. Substitution of the amino group at the 4-position of the meso-phenyl substituent resulted in a remarkable red shift in the absorption spectra and drastic enhancement of fluorescence intensity probably as a consequence of intramolecular CT interaction. These characteristics have been utilized to construct a cation-sensing system by appending a 1-aza-15-crown-5
Enlargement of the pi-electronic network of meso-meso, beta-beta, beta-beta triply linked diporphyrin has been exploited by preparing a corresponding dibenzo-fused porphyrin dimer that exhibits a perturbed absorption spectrum and a large two-photon absorption cross section.
The structures of metabolites produced in microgram quantities by enzymatic reductions with baker's yeast were analyzed using the crystalline sponge method. The X-ray data provided reliable structures for trace metabolites including their relative and absolute stereochemistries that are not fully addressed by conventional NMR and LC-MS analyses. Technically, combining two or more chromatographic purification techniques is essential because, unlike abundant synthetic compounds, extracted metaboli
The time capsule: A variety of guest molecules are stably trapped in networked coordination capsules up to 200 °C, which is above the boiling points of the guests. Networked capsules provide a distinctly different environment in the crystal form relative to that of pores, and are suitable for storing reactive molecules: Cyclopentadiene remains a monomer within the capsule even after heating, whereas dimerization through a Diels–Alder reaction takes place within the pore. Detailed facts of import
A coordination network composed of a mannose-based organic ligand and a sodium ion, 'sugar sponge', was synthesized for the crystalline sponge analysis of hydrophilic compounds. Owing to multiple hydrogen-bonding interactions, hydrophilic guests are firmly trapped in the 1-dimensional channel. The sugar sponge was utilized to analyze the structures of flexible alcohol and absolute configurations of chiral epoxides.
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