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Monitoring On‐Chip Pictet–Spengler Reactions by Integrated Analytical Separation and Label‐Free Time‐Resolved Fluorescence
Author(s) -
Ohla Stefan,
Beyreiss Reinhild,
Fritzsche Stefanie,
Glaser Petra,
Nagl Stefan,
Stockhausen Kai,
Schneider Christoph,
Belder Detlev
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101768
Subject(s) - pictet–spengler reaction , fluorescence , microfluidics , context (archaeology) , chemistry , chip , condensation reaction , nanotechnology , combinatorial chemistry , catalysis , materials science , computer science , organic chemistry , paleontology , telecommunications , physics , quantum mechanics , biology
High‐throughput screening for optimal reaction conditions and the search for efficient catalysts is of eminent importance in the development of chemical processes and for expanding the spectrum of synthetic methodologies in chemistry. In this context we report a novel approach for a microfluidic chemical laboratory integrating organic synthesis, separation and time‐resolved fluorescence detection on a single microchip. The feasibility of our integrated laboratory is demonstrated by monitoring the formation of tetrahydroisoquinoline derivatives by Pictet–Spengler condensation. After on‐chip reaction the products and residual starting material were separated enantioselectively on the same chip. On‐chip deep UV laser‐induced fluorescence detection with time‐correlated single photon counting was applied for compound assignment. The system was utilized to screen reaction conditions and various substrates for Pictet–Spengler reactions on‐chip. Finally, the microlab was successfully applied to investigate enantioselective reactions using BINOL‐based phosphoric acids as organocatalysts.