Self-assembly via intermolecular hydrogen-bonding between o-/m-/p -NH2 and BF2 groups on dipyrromethenes

AJi-Young Shin, Brian O. Patrick, David Dolphin

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, Canada BC V6T 1Z1ccomplishments


Boron difluoride dipyrromethenes bearing configurationally different amine groups on a meso phenyl ring were prepared and crystallized. The ortho and para amino groups allow the phenyl group to inductively release greater electron density into the dipyrromethenes resulting in relatively strong inter molecular hydrogen bonding with the terminal BF 2 groups, whereas the meta analog formed weaker hydrogen bonds. The intensities of the 1 H NMR peaks in concentrated solutions all increased with F decoupling