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Illinois State University

Carbaporphyrin

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Full-Text Articles in Physical Sciences and Mathematics

Synthesis Of Oxyquinoliziniporphyrins And Pyridoquinoliziniporphyrins, Emma Cramer Mar 2021

Synthesis Of Oxyquinoliziniporphyrins And Pyridoquinoliziniporphyrins, Emma Cramer

Theses and Dissertations

N-confused porphyrins are porphyrin analogues that introduce a nitrogen outside of the macrocyclic cavity. Two novel N-confused type porphyrins were targeted for this study. Both syntheses use the key intermediate 4-quinolizone. Previous studies of N-confused pyriporphyrin showed that the system is nonaromatic and resembles structurally analogous benziporphyrins. However, modifications to systems of this type can introduce aromatic characteristics. The first system targeted introduced a quinolizone subunit into a porphyrin system. Quinolizone contains a thermodynamically stable amide and this unit disrupts the aromatic pathway. However, dipolar resonance contributors can potentially reinstate some aromatic character. A quinolizone dialdehyde was condensed with tripyrranes …


Synthesis And Metalation Of Internally Alkylated Porphyrinoids, Alissa Nicole Latham Mar 2019

Synthesis And Metalation Of Internally Alkylated Porphyrinoids, Alissa Nicole Latham

Theses and Dissertations

The mechanism behind alkyl migration in palladium(II) benzocarbaporphyrins was investigated through the synthesis of a 23-methylcarbaporphyrin. It was found that palladium insertion led to methyl group migration to C21 and it is proposed that this occurs through an oxidative addition onto the palladium metal center, followed by a reductive elimination to transfer the methyl to the internal carbon. A similar rearrangement was observed when 23-methylcarbaporphyrin was reacted with [Rh(CO)2Cl]2 and resulted in the formation of a rhodium(III) complex containing a three-membered rhodacycle. The syntheses of rhodium(I) and rhodium(III) derivatives of other carbaporphyrins, including 21- and 22-methylbenzo-carbaporphyrins, were probed and four …


Synthesis And Characterization Of Naphthocarbaporphyrins And Related Systems, Eric Grabowski Sep 2015

Synthesis And Characterization Of Naphthocarbaporphyrins And Related Systems, Eric Grabowski

Theses and Dissertations

Carbaporphyrins are porphyrin analogs in which one of more of the pyrrole units have been replaced with a carbocyclic ring. In this project the cyclopentadiene ring replacing a pyrrole ring has been fused with a naphthalene ring. This is done in order to observe the effects of the naphthalene ring on the spectroscopic properties and reactivity.