The condensation reaction of fused dithienothiophene (DTT) diol with a core-modified tripyrrane led to the formation of acid and its concentration dependent products, sapphyrin and heptaphyrin. The single crystal X-ray analysis of sulphur and selenium heptaphyrin exhibits planar conformation owing to fusion. The experimental and theoretical calculations revealed the antiaromatic electronic structure of Hückel 4nπ.
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http://dx.doi.org/10.1039/c4cc05475j | DOI Listing |
Dalton Trans
April 2024
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A/2B Raja S.C Mullick Road, Jadavpur, Kolkata, West Bengal 700 032, India.
Retrosynthetic design and synthesis with structural isolation of two unprecedented core modified N-confused N-fused porphodimethene-like porphyrinoids possessing a [5.5.5.
View Article and Find Full Text PDFJ Chem Phys
April 2023
Laboratory of Theoretical Chemistry, Faculty of Chemistry and Biology, University of Santiago de Chile (USACH), 9170022 Santiago, Chile.
Chem Commun (Camb)
December 2020
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan.
Directly linked carbazole-based core-modified diporphyrin D2 and fused diporphyrin F2 were synthesized. These diporphyrins showed significant electronic interactions and conjugation allowing for redshifted near infrared (NIR) absorption and small HOMO-LUMO gaps as confirmed by NIR absorption spectroscopy, cyclic voltammetry (CV) measurements, and DFT calculations.
View Article and Find Full Text PDFLangmuir
April 2020
CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology (NCNST), Beijing 100190, China.
Scanning tunneling microscopy (STM) was utilized to disclose four novel core-modified rubyrin self-assembly behaviors on the highly-oriented pyrolytic graphite (HOPG) surface, of which NS-OR(1)/NSe-OR(2) had no phenanthrene pyrrole ring and NS-OR(3)/NSe-OR(4) had phenanthrene-fused pyrrole rings and meso-aryl substituents. It was discovered that the core-modified rubyrin could self-assemble into either face-on or edge-on monolayer structures selectively at the liquid/HOPG interface in different solvents. There was an obvious solvent-dependent self-assembly for NS-OR(3)/NSe-OR(4), which adopted an edge-on and face-on structure in 1-phenyloctane and 1-heptanoic acid solvents, respectively, whereas NS-OR(1)/NSe-OR(2) showed no obvious difference in the assembly structure, which both adopted a face-on structure in the two solvents.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
April 2019
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai, 200237, P. R. China.
A hybrid thia-norhexaphyrin comprising a directly linked N-confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner-annulated aromatic macrocycles. Oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone triggered a cleavage of the C-S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique π-conjugated products: a thiopyrrolo-pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur-free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H-thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions.
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