A novel smart supramolecular organic gelator exhibiting dual-channel responsive sensing behaviours towards fluoride ion via gel–gel states

Author(s): Hassan Mehdi ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Hongchang Pang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Weitao Gong ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Manivannan Kalavathi Dhinakaran ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Ali Wajahat ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Xiaojun Kuang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Guiling Ning ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2016

Journal: Organic & Biomolecular Chemistry

Publisher: Royal Society of Chemistry (RSC)

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Abstract

A smart organic gelator G-16 showed robust gelation as organogel OG and metallogel OG-Zn. Both OG and OG-Zn exhibited different sensing mode towards F ⁻. OG-Zn displayed unique selectivity for F ⁻ and formed OG-Zn-F gel while OG selectively formed OG-F gel via AIE.

Abstract

A novel smart supramolecular organic gelator G-16 containing anion and metal-coordination ability has been designed and synthesized. It shows excellent and robust gelation capability as a strong blue fluorescent supramolecular organic gel OG in DMF. Addition of Zn ²⁺ produced Zn ²⁺-coordinated supramolecular metallogel OG-Zn. Organic gel OG and organometallic gel OG-Zn exhibited efficient and different sensing behaviors towards fluoride ion due to the variation in self-assembling nature. Supramolecular metallogel OG-Zn displayed specific selectivity for fluoride ion and formed OG-Zn-F with dramatic color change from blue to blue green in solution and gel to gel states. Furthermore after directly addition of fluoride into OG produced fluoride containing organic gel OG-F with drastically modulation in color from blue to greenish yellow fluorescence via strong aggregation-induced emission (AIE) property. A number of experiments were conducted such as FTIR, ¹H NMR, and UV/Vis spectroscopies, XRD, SEM and rheology. These results revealed that the driving forces involved in self-assembly of OG, OG-Zn, OG-Zn-F and OG-F were hydrogen bonding, metal coordination, π–π interactions, and van der Waal forces. In contrast to the most anion responsive gels, particularly fluoride ion responsive gels showed gel–sol state transition on stimulation by anions, the gel state of OG and OG-Zn did not show any gel-to-sol transition during the whole F ⁻ response process.

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Stimuli-responsive supramolecular polymeric materials.

Xuzhou Yan, Feng Wang, Bo Zheng … (2012)

Supramolecular materials, dynamic materials by nature, are defined as materials whose components are bridged via reversible connections and undergo spontaneous and continuous assembly/disassembly processes under specific conditions. On account of the dynamic and reversible nature of noncovalent interactions, supramolecular polymers have the ability to adapt to their environment and possess a wide range of intriguing properties, such as degradability, shape-memory, and self-healing, making them unique candidates for supramolecular materials. In this critical review, we address recent developments in supramolecular polymeric materials, which can respond to appropriate external stimuli at the fundamental level due to the existence of noncovalent interactions of the building blocks.