Substituent Effects at the 5,10-Positions of Dianilinotripyrrins on Their Dimerization Dynamics

01 June 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


Control of the association behavior by the molecular design is one of the most essential benefits in artificial supramolecular systems. 1,14-Dianilinotripyrrin has recently emerged as a novel conjugated molecule which forms a double helix in non-polar solvents with the aid of multiple interstrand hydrogen bonding interactions. In this work, we investigated the substituent effects at the 5,10-positions of tripyrrin on their association dynamics. This study illuminated two key findings; 1) electronic tuning by the para-substituents reduce the entropic costs thereby slightly improve the association constants, and 2) ortho-substituents force the tripyrrin core to be relatively planar, which significantly decrease the association constant due to less feasible π-stacking.


hydrogen bonds
double helix
nitrogen heterocycles

Supplementary materials

Supporting Information
NMR spectra, Mass spectra, UV/Vis absorption, crystal structures, and theoretical calculations


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