Dynamic fluorescence imaging and controllable capture/release of guests based on thermo-responsive perylene-cyclodextrin conjugates

Abstract

In view of the fact that multivalent intermolecular noncovalent interactions are the main elements for the formation of phase separation, supramolecular entities are a type of multivalent system. However, the phase separation system based on single supramolecular molecules was limited. In this paper, two permethyl-β-cyclodextrin modified perylene monoamide derivatives (PMI-B-CD and PMI-N-CD) with modification of benzene and naphthalene groups at the bay position of perylene backbone were synthesized. Of interest, PMI-B-CD and PMI-N-CD showed a LCST effect due to a self-inclusion interaction between PMCD and the benzene or naphthalene groups in the bay position of perylene monoamide backbone. Dynamic confocal fluorescence imaging of PMI-B-CD and PMI-N-CD showed thermo-responsive phase separation process. It is surprised that PMI-B-CD and PMI-N-CD achieved thermo-responsive capture and release of aromatic guests. Dynamic phase separation and controllable capture and release of guests with thermo-responsive phase transition process are found, which opens a novel supramolecular principle of liquid-liquid transition.