Steric-Induced Fluorescence via Methyl Substitution in Chalcone Dyes

Christopher A. DeRosa, Garrett Wilkins

Abstract


Chemical research of luminescent dyes can have potential benefits in cell microscopy, optoelectronics and textiles. Luminescent chalcones have been studied extensively for their florescence properties and sensing capabilities, such as halochromism (pH), solvatochromism (polarity), and viscochromism (viscosity). Properties such as viscochromism can be utilized to sense the membrane viscosity in cells. To probe the viscochromic behavior of chalcones, bulky methyl-substituents were incorporated into the design of the chalcone to probe planarity, brightness and fluorescence turn-on based of environmental viscosity. This was achieved via Aldol condensation of aromatic ketones and para-(dimethylamino) benzaldehyde to incorporate a bulky methyl groups at an aromatic or vinyl positions. Synthesis of the derivatives was confirmed by 1H NMR, TLC and IR spectroscopy. Preliminary results indicate the dyes have yellow-green florescence in dichromomethane (Q.Y. ~12%), and aggregation induced emission (AIE) properties. This presentation will discuss the optical properties in solution, future directions and possible applications.


Keywords


Luminescence

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