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One‐Pot Synthesis of Highly Fluorescent Pyrido[1,2‐ a ]indole Derivatives through CH/NH Activation: Photophysical Investigations and Application in Cell Imaging
Author(s) -
Samala Srinivas,
Pallavi Pragyan,
Kumar Ravi,
Arigela Rajesh K,
Singh Gajendra,
Ampapathi Ravi Sankar,
Priya Amulya,
Datta Sunando,
Patra Abhijit,
Kundu Bijoy
Publication year - 2014
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.201404189
Subject(s) - indole test , fluorescence , quantum yield , chemistry , photochemistry , tandem , derivative (finance) , stereochemistry , materials science , physics , financial economics , economics , composite material , quantum mechanics
We describe a straightforward strategy for the synthesis of strongly fluorescent pyridoindoles by Pd‐catalyzed oxidative annulations of internal alkynes with C‐3 functionalized indoles through CH/NH bond activation in a one‐pot tandem process. Mechanistic investigations reveal the preferential activation of NH indole followed by CH activation during the cyclization process. Photophysical properties of pyridoindoles exhibited the highest fluorescence quantum yield of nearly 80 %, with emission color varying from blue to green to orange depending on the substructures. Quantum mechanical calculations provide insights into the observed photophysical properties. The strong fluorescence of the pyrido[1,2‐ a ]indole derivative has been employed in subcellular imaging, which demonstrates its localization in the cell nucleus.