Dicarba-closo-dodecaboranes (C2B10H12) and their derivative structures have drawn much interest in recent years. Their unique physical and chemical properties provide a wide usage area and potential functions such as catalyst or new pharmaceuticals. Boron Neutron Capture Therapy (BNCT) ,a binary therapy modality for treating cancer, is centered in the use of carboranes in medicinal chemistry allowing the destruction of target tumors with minimal damage to normal tissues[1].
Boron-dipyrromethene, abbreviated as BODIPY is composed of dipyrromethene and BF2 unit has attracted attention with its favorable physicochemical and spectral properties. BODIPY is an intensively colored fluorophore with high molar absorption coefficient, high fluorescence quantum yield, long fluorescence lifetime and excellent thermal and photostability[2].
Porphyrin[3] and BODIPY[4] functionalized carborane dyads are common in the literature, but conjugation of carborane together with porphyrin and BODIPY is unusual.
In this study, a new triad consisting of V-shaped BODIPY- o-carborane- prophyrin molecular array in which BODIPY and porphyrin units are substituted onto two adjacent carbon atoms of the central o-carborane is synthesized.This carborane based donor-acceptor-donor triad is characterized by 1H NMR, 13C NMR, 11B NMR and UV spectrophotometer.
1. Valliant, J.F., et al., The medicinal chemistry of carboranes. Coordination Chemistry Reviews, 2002. 232(1-2): p. 173-230.
2. Khan, T.K., et al., Boron dipyrrin-porphyrin conjugates. Coordination Chemistry Reviews, 2013. 257(15-16): p. 2348-2387.
3. Frixa, C., et al., Direct Cu(I)-catalysed coupling of a carborane to a meso-tetraphenylporphyrin. Tetrahedron Letters, 2002. 43(8): p. 1557-1559.
4. Jin, G.F., et al., BODIPY functionalized o-carborane dyads for low-energy photosensitization. Dalton Transactions, 2015. 44(6): p. 2780-2787.
