Document Type
Article
Publication Date
2025
Publication Title
ACS Omega
Keywords
alkyls, chemical structure, nuclear magnetic resonance spectroscopy, pyrroles, solutions
Abstract
Unsubstituted carbatripyrrins have previously been shown to be useful intermediates in the synthesis of benzocarbaporphyrins and related core-modified analogues. However, the absence of substituents often resulted in the formation of poorly soluble products. In this study, four examples alkyl substituted carbatripyrrins were constructed by base-catalyzed condensation of dihydrofulvenes with pyrrole aldehydes. Further reaction with a pyrrole dialdehyde in the presence of trifluoroacetic acid afforded a series of carbaporphyrins, while reactions with 2,5-furandicarboxaldehyde generated oxacarbaporphyrins. These results demonstrate that alkyl substituted carbatripyrrins are promising precursors to new carbaporphyrinoid structures.
Funding Source
This work was supported by the National Science Foundation under grants CHE-1855240 and CHE-2247214. NSF is also acknowledged for providing funding for the departmental NMR spectrometers (CHE-0722385) and mass spectrometer (CHE-1337497) under the Major Research Instrumentation (MRI) program. This article was published Open Access thanks to a transformative agreement between Milner Library and ACS.
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
DOI
10.1021/acsomega.5c07422
Recommended Citation
McLauchlan, I. A.; Overbey, B. K. X.; Smolczyk, T. J.; Woods, J. J.; Lash, T. D. Synthesis of Alkyl Substituted Carbatripyrrins and Their Application to the Preparation of Carbaporphyrins and Oxacarbaporphyrins. ACS Omega 2025, 10 (43), 51644–51656. https://doi.org/10.1021/acsomega.5c07422.
Comments
First published in ACS Omega (2025): https://doi.org/10.1021/acsomega.5c07422
Supporting information is available at https://pubs.acs.org/doi/10.1021/acsomega.5c07422.