Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

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作者
Rodrigues, A. Rita O. [1 ]
Carvalho, M. Solange D. [1 ,2 ]
Cardoso, J. André V. [1 ]
Calhelha, Ricardo C. [2 ]
Queiroz, Maria-João R.P. [2 ]
Coutinho, Paulo J.G. [1 ]
Castanheira, Elisabete M.S. [1 ]
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[1] Centro de Física (CFUM), Universidade Do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
[2] Centro de Química, Universidade Do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
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In this work, we were able to obtain the benzothieno[3,2-b]quinoline 1 and benzothieno[2,3-c]quinoline 2 using a new one-pot procedure from the reaction of the commercially available 3-bromobenzo[b]thiophene-2-carbaldehyde with 2-aminophenylpinacolborane under Suzuki coupling conditions using a stereochemically hindered ligand, 2-(cyclohexylphosphane)biphenyl and Ba(OH)2·8H2O as the base. Fluorescence properties of the benzothieno[3,2-b]quinoline 1 and the benzothieno[2,3-c]quinoline 2 were studied in solvents of different polarity. Both compounds exhibit a solvent sensitive emission, compound 1 being less fluorescent (ΦF;
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