Abstract
A novel series of bicyclic fluorescent heterocalixarenes – C‐alkyl coumarin[4]arenes – with built‐in chirality has been synthesized successfully in excellent yields under well‐optimized, improved reaction conditions. Further, structural elaboration (including π‐extension) of coumarin[4]arenes has been demonstrated by using Pd‐catalyzed Suzuki and Sonogashira cross‐coupling methods. All of these macrocycles are shown to possess averaged C4‐symmetric conformation in solution as opposed to the coumarin[4]arene tetratriflate derivative of C2 symmetry in the solid state. Finally, the macrocyclic coumarin[4]arenes reveal UV/near‐UV absorption and visible blue emission in solution. Such a visible blue luminescence of this macrocycle highlights its potential for sensing, bioimaging, and light‐emissive applications.
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