Carbohydrate sensing using a fluorescent molecular tweezer

Marcus D. Phillips, Thomas M. Fyles, Nicholas P. Barwell, Tony D. James
2009 Chemical Communications  
Experimental Materials Nuclear magnetic resonance spectra were run in CDCl 3 , CD 3 OD, DMSO-d 6 or CDCl 3 (0.8 ml) and CD 3 OD (2 drops). Where a Bruker AVANCE 300 was used 1 H spectra were recorded at 300.22 MHz and 1 H-13 C at 75.50 MHz. Where a Bruker AVANCE 400 was used 1 H spectra were recorded at 400.13 MHz and 13 C at 100.62 MHz. Chemical shifts (δ) are expressed in parts per million and are reported relative to the residual solvent peak or to tetramethylsilane as an internal standard
more » ... 1 H and 13 C spectra. The multiplicities and general assignments of the spectroscopic data are denoted as: singlet (s), doublet (d), triplet, (t), quartet (q), quintet (quin), doublet of doublets (dd), doublet of doublets of doublets (ddd), doublet of doublets of doublets of doublets (dddd), doublet of triplets (dt), triplet of triplets (tt), unresolved multiplet (m), apparent (app), broad (br) and aryl (Ar). Where stated the 13 C NMR spectra were subject to the polarisation that is nurtured during attached nucleus testing (PENDANT) technique, resulting in primary and tertiary carbon atoms having a different phase to secondary and quaternary carbon atoms. 1 The phases are reported as (+) positive phase and (-) negative phase. In certain instances the structural assignments reported for the 1 H NMR spectra were elucidated with the aid of correlated spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) NMR experiments. Infrared spectra were obtained (following internal background calibration) in the range 600-4000 cm -1 from KBr discs or CDCl 3 solutions using a Perkin-Elmer 1600 FT spectrometer. Characteristic absorption peaks are reported in wavenumbers (cm -1 ). Mass spectra were recorded by the EPSRC National Mass Spectrometry Service Centre, Swansea. Electrospray ionisation measurements were performed in positive ionisation mode (ES + ). High resolution ES + measurements were conducted on either a Finnigan MAT95 high resolution double focussing mass spectrometer or a MAT900 high resolution double focussing mass spectrometer with tandem ion trap. Capillary
doi:10.1039/b909230g pmid:19865648 fatcat:yuq7pyyyrffztkf6ccqgkejs64