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Expanding the Family of Fluorescent Coumarin[4]arenes: Improved Synthesis, π‐Extension, and Characterization
Author(s) -
Kumar Pawan,
Venkatakrishnan Parthasarathy
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901189
Subject(s) - sonogashira coupling , chemistry , fluorescence , coumarin , alkyl , photochemistry , chirality (physics) , heck reaction , bicyclic molecule , luminescence , absorption (acoustics) , combinatorial chemistry , derivative (finance) , conjugated system , coupling reaction , stereochemistry , organic chemistry , catalysis , aryl , palladium , polymer , physics , chiral symmetry breaking , optoelectronics , quantum mechanics , acoustics , financial economics , nambu–jona lasinio model , economics , quark
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 C 4 ‐symmetric conformation in solution as opposed to the coumarin[4]arene tetratriflate derivative of C 2 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.