Summary.
A new linear tetrapyrrole, with two dipyrrinones connected by a string of 5 carbons, was synthesized from two equivalents of a 9H-dipyrrinone and one of glutaryl dichloride. Unlike typical dipyrrinones, which are intermolecularly hydrogen bonded in the crystal and in CHCl3 solution, 1,3-bis-[2,3,7,8-tetraethyl-(10H)-dipyrrin-9-carbonyl]propane is a monomer in CHCl3, as determined by vapor phase osmometry (VPO) measurements. Its crystal structure determination revealed a folded conformation with a novel type of dipyrrinone to dipyrrinone intramolecular hydrogen bonding. Unexpectedly, the same conformation apparently persists in CHCl3 solution, as shown by 1H NMR spectroscopy.
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References
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Salzameda, N., Lightner, D. Intramolecular Hydrogen-Bonding in a C(10)-Exploded Bilirubinoid. Monatsh. Chem. 138, 237–244 (2007). https://doi.org/10.1007/s00706-007-0603-8
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DOI: https://doi.org/10.1007/s00706-007-0603-8