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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Generation of a new red fluorescent condensed hetero-aromatic compound:
1Okayama University Graduate School of Natural Science and Technology, Tsushima-Naka 3-1-1, Okayama 700-8530, Japan.
Abstract:
A coupling reaction of 5-methylbenz[b]acridin-12(5H)-one (MBA) with Zn and TiCl(4) provided a red fluorescent (FL) compound, as opposed to 5,5'-dimethyl-12,12'-bibenzo[b]acridylidene (DMBBA), probably through photochemical cyclization and aromatization by dehydrogenation of the overcrowded intermediate DMBBA. The structure of the red FL compound was assigned to 7,20-dimethyl-7,20-dihydro-7,20-diaza-naphto[a]dibenzo[j,q]perylene (DANDBP) and the fluorescence efficiency for DANDBP was determined to be 0.23 +/- 0.01.
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