Complex from ionic β-cyclodextrin polyrotaxane and sodium tetraphenylthiophenesulfonate: restricted molecular rotation and aggregation-enhanced emission

Abstract

ARTICLE RSC Adv.As restricted intramolecular rotation (RIR) is the main mechanism responsible for the aggregationinduced or -enhanced emission (AIE or AEE), we thereby use rigid polyrotaxane to impose effective RIR for an ionic water-soluble, AEE-active luminogen of sodium 4,4',4'',4'''-(thiophene-2,3,4,5tetrayl)tetrabenzenesulfonate (TPS). Jeffamine-included β-cyclodextrin (JA-included β-CD) with cationic ammonium terminals was used as rigid component to complex with sulfonate anions of TPS, resulting in iTP-CD-JA complex for characterization. Comparison is also made on complex of iTP-JA prepared from the complexation of TPS with the flexible JA chains. Without the incorporation of rigid β-CD rings, the iTP-JA complex is inferior to the iTP-CD-JA complex in the emission efficiency. The role of rigid template in imposing effective RIR on AEE-active luminogen is thus demonstrated in this study.ARTICLE 2 | RSC Adv., 2014 RSC Adv.

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.…”

“…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. 1 H NMR was used to explain, and it was found that the rigid 55 complex operated with more effective rotational restriction on the neighboring TPS luminogens than the flexible 54 complex, demonstrating that effective rotational restriction plays a more important role in controlling the emission efficiency of an AEE system than the content of the luminogen.…”

“…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. , …”

Polymeric AIE-based nanoprobes for biomedical applications: recent advances and perspectives

“…These polymeric micelles are formed through self-assembly of amphiphilic block copolymers in aqueous solution. [133][134][135][136][137][138][139][140][141] In 2010, Jen et al reported a non-covalent method for the coencapsulation of two AIE dyes (1,1,2,3,4,5-hexaphenylsilole (HPS) and/or bis(4-(N-(1-naphthyl) phenylamino)-phenyl)fumaronitrile (NPAFN)) into three amphiphilic block copolymers (Fig. 1).…”

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

“…When included in the cavity of g-CD, the amphiphilic AIEgens showed an enhanced monomer emission and a decreased aggregate emission. Recently, Jeffamine-included b-CD (JCD) with cationic ammonium terminals 65 was used as a rigid template to complex with the sulfonate anions of a tetraphenylthiophene derivative (TPS), resulting in an ionic complex, which emitted with superior emission intensity than complex from TPS and the exible Jeffamine. The role of rigid template in imposing effective RIR on AIEgen was demonstrated in this study.…”