Rigid Jeffamine-included polyrotaxane as hydrogen-bond template for salicylideneazine with aggregation-enhanced emission

Abstract

A Jeffamine-included polyrotaxane (JCD) was used as rigid template to impose effective rotational restriction on the AIE-active luminogen of 1,2-bis(2,4-dihydroxybenzylidene)hydrazine (CN4OH).

Sugar-Based Aggregation-Induced Emission Luminogens: Design, Structures, and Applications

“…Taking advantage of this, Hong's group prepared these kinds of complexes and used them to study the AIE mechanism by interaction with the negatively charged AIE molecules. 160,161 In one of their reported works, an anionic water-soluble AEE luminogen, TPS, was synthesized and mixed with H-JA and iCD-JA to form flexible and rigid complexes of 54 and 55, respectively (Figure 47). 160 Compared to 54, 55 had higher quantum efficiency even with lower concentration of TPS in the solid state.…”

“…Similarly, the JA-CD complex was mixed with an AIE molecule 56 in another system to research the relationship between molecular arrangement, restricted molecular rotation, and AIE emission based on the formation of a hydrogen bond. 106,161 In this work, Jeffamine-included β-CD (JCD) was prepared as a rigid template to mix with different amounts of 56 and formed AIE-active complexes with different 56/JCD ratio. As shown in Figure 48, for the blends with less 56 than Considering this phenomenon, these kinds of materials were always widely used as smart sensors or used in some special stimuli response systems in biological research such as drug delivery, controlled release, and targeted cell imaging.…”

“…As a widely used host molecule, β-CD has host–guest interaction with lots of guest materials with suitable size in which the diamino-terminated poly­(propylene glycol) (Jeffamine, JA) with two positive charges on its terminal can form a rigid complex with β-CD by inserting its main chain into the cavity of the cyclodextrin rings. Taking advantage of this, Hong’s group prepared these kinds of complexes and used them to study the AIE mechanism by interaction with the negatively charged AIE molecules. , …”

“…Similarly, the JA-CD complex was mixed with an AIE molecule 56 in another system to research the relationship between molecular arrangement, restricted molecular rotation, and AIE emission based on the formation of a hydrogen bond. , In this work, Jeffamine-included β-CD (JCD) was prepared as a rigid template to mix with different amounts of 56 and formed AIE-active complexes with different 56 /JCD ratio. As shown in Figure , for the blends with less 56 than JCD, 56 was dispersed by the majority of JCDs and formed a hydrogen bond with JCDs; the rotational restriction of 56 by JCDs played the most important role in controlling the emission of the complex.…”

“…(B) Transformation of molecular arrangements upon increasing 56 in the blends. Adapted with permission from ref . Copyright 2015 The Royal Society of Chemistry.…”