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Issue 8, 2013
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Functionalized 3-pyrrolyl boron-dipyrromethenes

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Abstract

A series of mono-functionalized 3-pyrrolyl boron-dipyrromethenes containing functional groups such as bromo, formyl, cyano, nitro and trimethylsilylacetylene groups at the α-position of the uncoordinated pyrrole group were synthesized. Further to show the use of functionalized 3-pyrrolyl BODIPY, we treated α-bromo BODIPY with four different boronic acids such as phenyl, biphenyl, phenylacetyl and thienyl boronic acids under mild Pd(0) coupling conditions to afford α-aryl substituted 3-pyrrolyl BODIPYs. α-Dipyrromethanyl substituted 3-pyrrolyl BODIPY was synthesized by treating α-formyl 3-pyrrolyl BODIPY with pyrrole in the presence of TFA in CHCl3. The 3-pyrrolyl BODIPY appended with BODIPY (BODIPY dyad) at the α-position of uncoordinated pyrrole was synthesized by oxidizing 3-dipyrromethanyl BODIPY with DDQ followed by complexation with BF3·Et2O. All compounds were characterized by HRMS mass, NMR, absorption, electrochemical and fluorescence techniques. The spectral studies indicated that the presence of substituent at the α-position of uncoordinated pyrrole of 3-pyrrolyl BODIPY alter the electronic properties of the BODIPY core. The photophysical studies on BODIPY dyad indicated a possibility of energy transfer from the appended BODIPY unit to the 3-pyrrolyl BODIPY unit in BODIPY dyad.

Graphical abstract: Functionalized 3-pyrrolyl boron-dipyrromethenes

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Publication details

The article was received on 24 Oct 2012, accepted on 11 Dec 2012 and first published on 12 Dec 2012


Article type: Paper
DOI: 10.1039/C2RA22618A
RSC Adv., 2013,3, 2736-2745

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    Functionalized 3-pyrrolyl boron-dipyrromethenes

    T. Kaur, V. Lakshmi and M. Ravikanth, RSC Adv., 2013, 3, 2736
    DOI: 10.1039/C2RA22618A

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