Solvatochromic probes for detecting hydrogen-bond-donating solvents

Ryan F. Landis, Mahdieh Yazdani, Brian Creran, Xi Yu, Vikas Nandwana, Graeme Cooke, Vincent M. Rotello
2014 Chemical Communications  
Hydrogen bonding heavily influences conformations, rate of reactions, and chemical equilibria. The development of a method to monitor hydrogen bonding interactions independent of polarity is challenging as both are linked. We have developed two solvatochromic dyes that detect hydrogen-bond-donating solvents. The unique solvatochromism of the triazine architecture has allowed the development of probes that monitor hydrogen-bond-donating species including water. Scheme 1 Synthetic steps to (a)
more » ... AT and (b) AMADAT. † Electronic supplementary information (ESI) available: Quantum yield of MADAT in DCM and methanol. Emission of MADAT in phenol and trifluoroethanol. AMADAT emission in various solvents. Linear correlation between concentration of thymine 1 and fluorescence intensity. Addition of N-Me thymine 2 to MADAT in DCM. Linear relation between water concentration and fluorescence intensity. Concentration versus emission plots for MADAT and AMADAT. See
doi:10.1039/c4cc00805g pmid:24667987 fatcat:5gylh5vzfncetohpdpyojww4r4