Radially π-Extended Pyrrole-Fused Azacoronene: A Series of Crystal Structures of HPHAC with Various Oxidation States
Yoshiki Sasaki, Masayoshi Takase, Nagao Kobayashi, Shigeki Mori, Keishi Ohara, Tetsuo Okujima, Hidemitsu Uno
Abstract
Radially π-extended hexapyrrolohexaazacoronene (HPHAC 2) was synthesized in two steps with 2,5-di-tert-butyl-acenaphtho[1,2-c]pyrrole and hexafluorobenzene. Like its parent HPHAC 1a, 2 exhibited reversible oxidation behavior. Crystal structures of not only the neutral and dicationic compounds but also the radical cation were all revealed. While analyzing its peculiar structure, the formation of a 1:1 complex with C60 was observed in solution by NMR and absorption analyses. The spectroscopic analyses of 2 and 1a were performed based on magnetic circular dichroism and theoretical calculations.
Topics & Concepts
ChemistryPyrroleCrystal structureCrystallographyHexafluorobenzeneAbsorption (acoustics)Crystal (programming language)Circular dichroismPhotochemistryMoleculeOrganic chemistryComputer sciencePhysicsProgramming languageAcousticsPorphyrin and Phthalocyanine ChemistrySynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent Materials