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Synthesis and Studies of Aza‐BODIPY‐Based π‐Conjugates for Organic Electronic Applications
Author(s) -
Khan Tamanna K.,
Sheokand Preeti,
Agarwal Neeraj
Publication year - 2014
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.201301300
Subject(s) - bodipy , chemistry , photochemistry , absorption (acoustics) , conjugated system , fluorescence , absorption spectroscopy , electrochemistry , quantum yield , suzuki reaction , chloroform , palladium , organic chemistry , polymer , materials science , catalysis , physics , electrode , quantum mechanics , composite material
Aza‐boron‐dipyromethene (aza‐BODIPY) derivatives 1 – 6 were synthesized for the first time by employing the palladium catalyzed Suzuki–Miyaura coupling on dibromo‐aza‐BODIPY. Photophysical and electrochemical properties of these compounds were studied in solution. Absorption and emission maxima were observed in the near‐infrared (NIR) region and were found to extend up to 754 and 751 nm, respectively. NIR fluorescence quantum yields in chloroform were as high as 0.45. Optical band gaps were measured from the onset of absorption spectra in thin films and were found to be low (ca. 1.2–1.4 eV). Electrochemical studies provided insight into the reduction potentials of these compounds and consequently the electron affinity (EA). High electron affinity (ca. 4.5) was observed for these dyes. NIR absorption and emission, good quantum yield, and high electron affinity of these compounds promise their applications in microscope imaging and optoelectronic devices, mainly in solar cells and field‐effect transistors.