Axial chiral bisbenzophenazines: solid-state self-assembly via halide hydrogen bonds triggered by linear alkanes.

ABSTRACT: An axial chiral tetrachlorinated bisbenzo[a]phenazine has been discovered that undergoes an alkane-induced shift in the solid state from a disordered amorphous form to an ordered polycrystalline form. This phase transition is caused by the formation of pores that accommodate linear alkanes of varying lengths with a very strong affinity as judged by differential scanning calorimetry. Single crystal X-ray structure analysis revealed that a series of weak phenolic OH···Cl hydrogen bonds dictates the pore structure. These weak interactions can be disrupted mechanically, causing the material to revert to the amorphous form. Notably, the interchange between the amorphous and crystalline forms is readily reversible and is easily observed by characteristic colorimetric changes. Measurements via ph

SUBMITTER: Metz AE 

PROVIDER: S-EPMC4353019 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature