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Bent Dithienoporphyrin(2.1.2.1): Synthesis, Structure, Optical and Electronic Properties, and Metal Complexation

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JOURNAL OF ORGANIC CHEMISTRY
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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02520

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Four kinds of isomeric dithienoporphyrins(2.1.2.1) were synthesized using two di(1H-pyrrolo-2-yl)thiophenes as building blocks and two arylaldehydes under mild acid-catalyzed conditions. The conformation and properties of the dithienoporphyrins(2.1.2.1) were investigated using various spectroscopic techniques and theoretical calculations. The incorporation of thiophene subunits resulted in a more planarized molecular structure, and the dithienoporphyrin(2.1.2.1) acted as a ligand for metal ions, leading to bent molecular conformations.
Four kinds of isomeric dithienoporphyrins(2.1.2.1) were prepared using two di(1H-pyrrolo-2-yl)thiophenes as building blocks and two arylaldehydes under mild acid-catalyzed conditions. The molecular conformation and optical and electronic properties of dithienoporphyrins(2.1.2.1) were investigated by NMR spectroscopy, X-ray diffraction, UV-vis absorption spectroscopy, electrochemical measurements, and theoretical calculations. The crystal structure of [2,3]F5TP has the largest angle between the two planes of the dipyrrin units among dibenzo-/dinaphthoporphyrins(2.1.2.1). This result indicates that the incorporation of thiophene subunits into a porphyrin(2.1.2.1) macrocycle results in the alteration of the molecular geometry to a more planarized structure. Dithienoporphyrin(2.1.2.1) is found to act as a ligand that can form metal complexes with nickel(II), copper(II), and palladium(II) ions. The molecular structures of the dithienoporphyrin(2.1.2.1) metal complexes exhibited bent molecular conformations. The red-shifted absorption, reversible redox processes, and theoretical calculations indicated that the electronic properties of the dithienoporphyrin(2.1.2.1) metal complexes are controlled by the inserted metal ions.

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