Phosphorescent Dimesitylboryl-Appended Iridium(III) Complex for Fluoride Anion Sensing

作者: Yinan Li , Myung-Ho Hyun

DOI: 10.5012/BKCS.2011.32.11.4125

关键词:

摘要: Owing to the importance of fluoride anion (F−) in treatment osteoporosis and dental care, recognition sensing is attracting attention. Many chemosensors containing (thio) ureas, amides, pyrrole, imidazolium ring have been prepared date. Those usually form strong hydrogen bonds between their N-H hydrogens anion. Recently, tri-coordinate organoboron compounds such as dimesitylboryl [B(Mes)2] found achieve highly efficient detection using specific Lewis acid-base interaction. Fluoride based on boron moiety B(Mes)2 bind with afford B-F interaction, which can change lowest excited state or block intramolecular charge transfer. Thereby, photophysical properties be changed. However, output signals selective absorption and/or fluorescence. Nowadays, phosphorescent also developed for anions since first sensor reported by Gabbai et al. Phosphorescent are quite attractive because relatively long life time phosphorescence eliminate interference shorter-lived background fluorescence scatterring light present biological samples. Among various types phosphors, cyclometalated iridium(III) complexes that used, example, an dopant organic emitting diodes (OLEDs) a chemosensor mercuric ion excellent electrochemical properties. only few complex reported. In this paper, we report synthesis novel complex, Ir(p-B-ppy)2picolinate (1), where p-B-ppy 2-(4-(dimesitylboryl)phenyl)pyridine, its application A multi-step synthetic pathway leading (1) shown Scheme 1. The main ligand (2), was Suzuki coupling 4-bromophenylboronic acid 2-bromopyridine then substitution bromo group via procedure reported, treated chloride trihydrate mixed solvent 2-ethoxyethanol water iridium chloride-bridged dimer 3, [(p-B-ppy)2IrCl]2. 3 picolinic presence sodium carbonate (1). UV-vis photoluminescence spectra Ir(p-B-

参考文章(28)
Pavel Anzenbacher,, Daniel S. Tyson, Karolina Jursíková, Felix N. Castellano, Luminescence lifetime-based sensor for cyanide and related anions. Journal of the American Chemical Society. ,vol. 124, pp. 6232- 6233 ,(2002) , 10.1021/JA0259180
Mamta Chahar, Pramod S. Pandey, Design of steroid-based imidazolium receptors for fluoride ion recognition Tetrahedron. ,vol. 64, pp. 6488- 6493 ,(2008) , 10.1016/J.TET.2008.04.065
Chia-I Lin, Srinivasan Selvi, Jim-Min Fang, Pi-Tai Chou, Chin-Hung Lai, Yi-Ming Cheng, Pyreno[2,1-b]pyrrole and bis(pyreno[2,1-b]pyrrole) as selective chemosensors of fluoride ion: a mechanistic study. Journal of Organic Chemistry. ,vol. 72, pp. 3537- 3542 ,(2007) , 10.1021/JO070169W
Yinan Li, Ung-Chan Yoon, Myung-Ho Hyun, Phosphorescent Azacrown Ether-appended Iridium (III) Complex for the Selective Detection of Hg 2+ in Aqueous Acetonitrile Bulletin of The Korean Chemical Society. ,vol. 32, pp. 122- 126 ,(2011) , 10.5012/BKCS.2011.32.1.122
Duraisamy Saravanakumar, Nallathambi Sengottuvelan, Muthusamy Kandaswamy, Paduthapillai Gopal Aravindan, Devadoss Velmurugan, Amide-nitrophenyl based colorimetric receptors for selective sensing of fluoride ions Tetrahedron Letters. ,vol. 46, pp. 7255- 7258 ,(2005) , 10.1016/J.TETLET.2005.08.045
Shawn C McCleskey, Axel Metzger, Chris S Simmons, Eric V Anslyn, Competitive indicator methods for the analysis of citrate using colorimetric assays Tetrahedron. ,vol. 58, pp. 621- 628 ,(2002) , 10.1016/S0040-4020(01)01093-6
Wei Tan, Deqing Zhang, Zhuo Wang, Caiming Liu, Daoben Zhu, 4-(N,N-Dimethylamine)benzonitrile (DMABN) derivatives with boronic acid and boronate groups: new fluorescent sensors for saccharides and fluoride ion Journal of Materials Chemistry. ,vol. 17, pp. 1964- 1968 ,(2007) , 10.1039/B618183J
Christoph Ulbricht, Beatrice Beyer, Christian Friebe, Andreas Winter, Ulrich S. Schubert, Recent Developments in the Application of Phosphorescent Iridium(III) Complex Systems Advanced Materials. ,vol. 21, pp. 4418- 4441 ,(2009) , 10.1002/ADMA.200803537
Ramón Martínez-Máñez, Félix Sancenón, Fluorogenic and chromogenic chemosensors and reagents for anions. Chemical Reviews. ,vol. 103, pp. 4419- 4476 ,(2003) , 10.1021/CR010421E
Purnandhu Bose, Pradyut Ghosh, Visible and near-infrared sensing of fluoride by indole conjugated urea/thiourea ligands Chemical Communications. ,vol. 46, pp. 2962- 2964 ,(2010) , 10.1039/B919128C