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Published on: August 19, 2013
A Benzothiazinonecopillar[5]arene Derivative: Synthesis, Supramolecular Aggregation, and Fluorogenic Detection of
Subrata Ranjan Dhara1, Kumaresh Ghosh1
1Department of Chemistry, University of Kalyani, Kalyani741235, India.
A novel copillar[5]arene, HBTP, selectively detects basic analytes like DBU using fluorescence. This macrocycle shows unique responses in solution and solid states, enabling sensitive DBU detection.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Analytical Chemistry
Background:
- C Pillar[5]arenes are macrocyclic hosts with tunable cavities.
- Benzothiazinone motifs introduce unique electronic and binding properties.
- Molecular recognition of basic analytes is crucial for sensing applications.
Purpose of the Study:
- Synthesize and characterize a new copillar[5]arene, HBTP, incorporating a benzothiazinone unit.
- Investigate the molecular recognition capabilities of HBTP towards various basic analytes.
- Explore the potential of HBTP as a selective fluorescent sensor for basic compounds.
Main Methods:
- Synthesis and structural characterization of HBTP.
- Fluorescence spectroscopy to study host-guest interactions.
- Detection limit determination for target analytes.
- Solid-state analysis using paper strips.
- Redox activity studies.
- Theoretical calculations (DFT) to understand electronic properties.
Main Results:
- HBTP exhibits supramolecular assemblies in the solid state.
- HBTP shows a ratiometric fluorescent response to basic analytes via deprotonation.
- Selective detection of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) in acetonitrile and aqueous acetonitrile.
- Low detection limit for DBU (1.38 × 10-7 M in CH3CN).
- Distinct solid-state emission and selective DBU detection on paper strips.
- Redox activity and theoretical corroboration of electronic properties.
Conclusions:
- HBTP is a structurally unique copillar[5]arene with effective molecular recognition abilities.
- HBTP serves as a selective and sensitive fluorescent sensor for DBU.
- The macrocycle demonstrates versatile sensing capabilities in both solution and solid states.
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