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Synthesis and Properties of 5,7‐Dihydropyrido[3,2‐ b :5,6‐ b′ ]diindoles
Author(s) -
Hung Tran Quang,
Thang Ngo Ngoc,
Hoang Do Huy,
Dang Tuan Thanh,
Ayub Khurshid,
Villinger Alexander,
Lochbrunner Stefan,
Flechsig GerdUwe,
Langer Peter
Publication year - 2015
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.201403035
Subject(s) - chemistry , electrochemistry , quantum chemical , molecule , coupling (piping) , coupling reaction , combinatorial chemistry , suzuki reaction , computational chemistry , organic chemistry , catalysis , electrode , palladium , mechanical engineering , engineering
5,7‐Dihydropyrido[3,2‐ b :5,6‐ b′ ]diindoles were prepared by a highly efficient two‐step synthesis that involved a site‐selective Suzuki coupling reaction of 2,3,5,6‐tetrabromopyridine and a subsequent Pd‐catalyzed cyclization that proceeded through a twofold C–N coupling reaction with aromatic and aliphatic amines. With the exception of the parent molecule, which was described in a patent without any characterization data, the 5,7‐dihydropyrido[3,2‐ b :5,6‐ b′ ]diindoles are a new chemical entity. Their electrochemical and photochemical properties were investigated. These pyridodiindoles show promising fluorescence properties with good quantum yields and interesting electrochemical behavior. The optical and electronical properties were analyzed and explained by using DFT calculations.