Development of Ion Chemosensors Based on Porphyrin Analogues
Top Cited Papers
- 14 April 2016
- journal article
- review article
- Published by American Chemical Society (ACS) in Chemical Reviews
- Vol. 117 (4), 2203-2256
- https://doi.org/10.1021/acs.chemrev.6b00021
Abstract
Sensing of metal ions and anions is of great importance because of their widespread distribution in environmental systems and biological processes. Colorimetric and fluorescent chemosensors based on organic molecular species have been demonstrated to be effective for the detection of various ions and possess the significant advantages of low cost, high sensitivity, and convenient implementation. Of the available classes of organic molecules, porphyrin analogues possess inherently many advantageous features, making them suitable for the design of ion chemosensors, with the targeted sensing behavior achieved and easily modulated based on their following characteristics: (1) NH moieties properly disposed for binding of anions through cooperative hydrogen-bonding interactions; (2) multiple pyrrolic N atoms or other heteroatoms for selectively chelating metal ions; (3) variability of macrocycle size and peripheral substitution for modulation of ion selectivity and sensitivity; and (4) tunable near-infrared emission and good biocompatibility. In this Review, design strategies, sensing mechanisms, and sensing performance of ion chemosensors based on porphyrin analogues are described by use of extensive examples. Ion chemosensors based on normal porphyrins and linear oligopyrroles are also briefly described. This Review provides valuable information for researchers of related areas and thus may inspire the development of more practical and effective approaches for designing high-performance ion chemosensors based on porphyrin analogues and other relevant compounds.Keywords
Funding Information
- State Administration of Foreign Experts Affairs (B16017)
- Ministry of Education of the People's Republic of China (B16017)
- Ministry of Science and Technology of the People's Republic of China (2013CB733700)
- Natural Science Foundation of Jiangsu Province (BK20140593)
- National Natural Science Foundation of China (21421004, 21472047, 91227201)
- State Key Laboratory for Chemo/Biosensing and Chemometrics, Hunan University (2014002)
This publication has 100 references indexed in Scilit:
- N,N-di(2-pyridylmethyl)amino-modified porphyrinato zinc complexes. The “ON–OFF” fluorescence sensor for Fe3+Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013
- Decoration of Gold Nanoparticles by a Double‐Armed Calix[4]pyrrole: A Receptor‐Decorated Nanoensemble for Anion Sensing and ExtractionChemistry – A European Journal, 2013
- A novel Bodipy-Dipyrrin fluorescent probe: Synthesis and recognition behaviour towards Fe (II) and Zn (II)Dyes and Pigments, 2012
- A fluoride selective dipyrromethane-TCNQ colorimetric sensor based on charge-transferTalanta, 2011
- Oligopyrrole Macrocycles: Receptors and Chemosensors for Potentially Hazardous MaterialsChemistry – A European Journal, 2011
- NIR dyes for bioimaging applicationsCurrent Opinion in Chemical Biology, 2010
- An optical sensor for mercury ion based on the fluorescence quenching of tetra(p-dimethylaminophenyl)porphyrinAnalytica Chimica Acta, 2009
- Benzene‐, Pyrrole‐, and Furan‐Containing Diametrically Strapped Calix[4]pyrroles—An Experimental and Theoretical Study of Hydrogen‐Bonding Effects in Chloride Anion RecognitionAngewandte Chemie, 2008
- A porphyrin derivative containing 2-(oxymethyl)pyridine units showing unexpected ratiometric fluorescent recognition of Zn2+ with high selectivityAnalytica Chimica Acta, 2008
- meso‐Substituted Aromatic 34π Core‐Modified Octaphyrins: Syntheses, Characterization and Anion Binding PropertiesChemistry – A European Journal, 2003