Abstract
Owing to the selective recognition ability, exceptional biocompatibility, water solubility, non-toxicity, economically inexpensive, commercial availability, and easy functionalization, cyclodextrins (CDs) act as the main building blocks for the creation of beautifully simple yet much effective supramolecular architectures of fundamental interest. Over the past few decades, CDs have engrossed a noteworthy interest in the scientific community because of their usage in the development of chemical sensors via molecular recognition phenomenon. Bearing the delightful sensing capability of CDs in mind, herewith, we envisioned to disclose the recent developments in the sensing of diverse biologically significant small molecules by CDs through colorimetric, fluorescence, electrochemical, and potentiometric response. Sensing events and corresponding distinguishing optical features in cyclodextrin-based monomers, dimers, clusters, and nano-assemblies have been elaborated in detail. The authors are of the opinion that this chapter will offer new dimensions to supramolecular sensors in general and CDs-based sensors in particular.
Keywords
- cyclodextrins
- host-guest interaction
- molecular recognition
- small molecules
- colorimetric and electrochemical sensors
1. Introduction
Basically, the host-guest non-covalent interaction is the major subtopic of supramolecular chemistry, which succors us to realize the recognition of guest entities, particularly through non-covalent supramolecular interactions [1, 2]. In recent years, the supramolecular host molecules, such as cyclophanes, crown ethers, cryptands, calix[n]arenes, calix[n]pyrroles, cucurbiturils, and cyclodextrins, have drawn an enormous interest of the scientific community worldwide because of their exceptional signatures, particularly molecular recognition and sense of specific analytes, and still much new chemistry with these old macrocycles is to be explored [3, 4, 5, 6, 7]. Among the above-mentioned host architectures, the naturally occurring cyclodextrins (CDs) are regarded as most essential by virtue of their selective recognition capability, exceptional biocompatibility, water solubility, non-toxicity, economically inexpensiveness, commercial availability, and easy-functionalization [8]. With the aid of host-guest chemistry, the CDs have found a range of applications in various fields of science and technology
The CDs are cyclic oligosaccharides-based seminatural products, mostly comprising of 6−8 units (
As can be straightforwardly inspected from the scientific publications appearing in the literature, the domain of chemical sensors in general and CD-based sensors in particular are rapidly progressing and strengthening their roots in various aspects of our day-to-day life besides bringing a revolution in diverse arena of science and technology [16]. Keeping these facts in mind and also to expose the importance of sensory materials based on CDs; in this meticulous review chapter, we indented to highlight the recent developments in addition to the conceptual background of CD-based chemical sensors. Hopefully, the readers will enjoy this draft and will for sure be further to explore these old yet new types of macromolecular platforms to an advanced level.
2. Chromophore-appended cyclodextrins as classical chemical sensors
Among a variety of chemical sensors, the optical chemosensors are truly interesting and advantageous [17]. This can be ascribed to the fact that optical variations
Keeping in consideration, the fact that microenvironment of the utilized chromophores offer changes in color as well as fluorescence pattern, and to get optimum output, researchers globally have functionalized the CDs with a variety of dyes besides the fluorescent moieties [19, 20]. Using chromophore-appended CDs, the detection of a range of hydrophobic guest molecules inside the hydrophobic cavities has extensively been studied in recent years. However, a plethora of chromophore-appended CDs have been constructed and their sensing activities have also been accomplished by several research groups worldwide. But, the pioneering work in this field has been revealed by Ueno and teammates; they reported many CD-based fluorescent chemical sensors through the installation of diverse fluorophores (dansyl, pyrene, anthracene,
On the other hand, the same group has also constructed various colorimetric indicator dyes (
Sulfur dioxide is widely used as a preservative and antioxidant in the food and beverage industries. Thus, constructing sulfur dioxide sensors is of utmost significance in food and analytical chemistry. In this regard, Levine and co-workers have modified the Whatman filter paper with
3. Metallocyclodextrin-based chemical sensors
The metallocyclodextrin-based CDs have been developed by various research groups and utilized in the field of chemical sensors [29, 30]. To this line, ligands consisting of the metal binding sites, for example, crown ether, diethylenetriaminepentaacetate (DTPA), and ethylenediaminetetraacetate (EDTA), have successfully been reported. Noticeably, among the various metal ions, lanthanide metal ions (Eu2+ & Tb2+) are primarily used in the fabrication of metallocyclodextrin-based chemical sensors by virtue of the fact that they exhibit strong fluorescence and also showed the longer lifetimes [31]. Out of various sensing mechanisms, absorption energy transfer emission (AETE) has been found responsible for the sensing of metallocyclodextrins. This sensing mechanism preliminary involves the excitation of light harvesting guest molecule
Liu
4. Cyclodextrin-based supramolecular systems as chemical sensors
Design and construction of the supramolecular architectures utilizing CD units as the key building blocks have attracted an increasing curiosity in the development of chemical sensors [39, 40]. In comparison with CD monomers, the covalently coupled CD-dimers and CD-trimers possess bigger hydrophobic cavities to accommodate the large guest molecules, which make them ideal candidates for chemical sensing. In this context, Ueno and co-workers have reported the
Interestingly, sensing conjugates of CDs with macrocyclic hosts employing cooperative molecular recognition phenomenon have also been fabricated by various researchers across the world. In this context, Hayashita and teammates have developed a highly selective hybrid molecular conjugate (
The research group of Anderson has used
5. Cyclodextrin-based electrochemical sensors
Owing to the chief and portable instrumentation, rapid analysis, and high selectivity, as well as sensitivity, in recent years, electrochemical sensing has engrossed a significant courtesy in the recognition of biomolecules and environmentally hazardous pollutants [51, 52, 53]. Cyclodextrin-based functional materials have proven to be highly useful in the domain of electrochemical sensing in past decade [54, 55]. These functional materials mainly include CD-based carbon nanomaterials: carbon nanotubes (CNTs), graphene, and conducting polymers. Nowadays, developing the CD-based conducting polymers for the purpose of electrochemical sensing is considered a hot subject of research interest [56]. This is due to the fact that CD-based conducting polymers pasted on electrodes
In the context of CD-based carbon nanomaterials, Huang’s research group has modified glassy carbon electrode (GCE) by single-walled CNT (SWCNT) and pyrene functionalized
Recognition of chiral enantiomers
Over the past several years, diverse CD-based potentiometric sensors working through electrochemical means have fruitfully been developed, which find significant applications in medicine, agriculture, environmental monitoring, pharmaceutical sciences, and industries [65, 66]. In this context, Lenik and teammates have developed functionalized
6. Cyclodextrin-based polymers as chemical sensors
Due to widespread applicability of
As coumarin and pyrene scaffolds are of great importance, owing to their vital role in biological systems and sensing arena as well [73]. In this regard, Ueno’s group has synthesized
On the other hand, quite recently, Badiei and co-workers have established a
7. Cyclodextrin-nanocarbon hybrids as chemical sensors
Over the past several decades, carbon nanomaterials for instance carbon nanotubes, fullerene and nanodiamonds, and other polyaromatic hydrocarbons because their unique electrical, structural, and mechanical properties have riveted a significant interest of the researchers across the globe to meet the challenge of constructing the CD-based sensors through hybridization with carbon nanomaterials [78, 79, 80, 81]. In this context, Fujita and Yuan
8. Cyclodextrin-nanoparticle hybrids as chemical sensors
In recent years, scientific community has exploited the unique property of gold nanoparticle aggregation in the design and construction of various optical sensory devices where the sensing mechanism is perceived through color variation from red to purple/blue. In this regard, Kaifer and teammates have constructed
9. Conclusions and outlook
In summary, this chapter discusses the conceptual background as well as evolutionary developments of chemical sensing in cyclodextrin-based monomers, dimers, clusters, and nano-assemblies with a detection limit up to μM/nM level. The sensing event of various guest molecules
Acknowledgments
We are highly thankful to DST-SERB New Delhi for financial support (Project File no. ECR/2017/000821). I. A. R. thanks CSIR, New Delhi, for the award of the JRF and SRF. A.H. thanks UGC for non-NET fellowship. R. A. thanks Jamia Millia Islamia, New Delhi, for providing the necessary research facilities.
Conflicts of interest
The authors declare no conflicts of interest.
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