Research Highlights

  • Research Highlights
  • /
  • Pyridyl-Amides as a Multimode Self-assembly Driver for the Design of a Stimuli Responsive π-Gelator

Pyridyl-Amides as a Multimode Self-assembly Driver for the Design of a Stimuli Responsive π-Gelator

K. K. Kartha, V. K. Praveen, S. S. Babu, S. Cherumukkil and A. Ajayaghosh*

An oligo(p-phenylenevinylene) (OPV) derivative connected to pyridyl end groups through an amide linkage (OPV-Py) resulted in a multistimuli-responsive pi-gelator. When compared to the corresponding OPV -gelator terminated by a phenyl-amide (OPV-Ph), the aggregation properties of OPV-Py were found to be significantly different, leading to multistimuli gelation and other morphological properties. The pyridyl moiety in OPV-Py initially interferes with the amide H-bonded assembly and gelation, however, protonation of the pyridyl moiety with trifluoroacetic acid (TFA) facilitated the formation of amide H-bonded assembly leading to gelation, which is reversible by the addition of N,N-diisopropyethylamine (DiPEA). Interestingly, addition of Ag+ ions to a solution of OPV-Py facilitated the formation of a metallo-supramolecular assembly leading to gelation. Surprisingly, ultrasound-induced gelation was observed when OPV-Py was mixed with a dicarboxylic acid (A1). A detailed study using different spectroscopic and microscopic experimental techniques revealed the difference in the mode of assembly in the two molecules and the multistimuli-responsive nature of the OPV-Py gelation.

Chem.Asian J. 2015, 10, 2250–2256. (Part of Special Board Member Issue Published on the Occasion of 10th Anniversary of Chem. –Asian J.)

Full Text Link:http://dx.doi.org/10.1002/asia.201500331(Open Access)