Symmetry breaking intramolecular charge transfer (ICT) that is stabilized in polar environments has been observed in systems ranging from the photosynthetic reaction center to 9,9'-bianthracene.  The ability to charge transfer is important for high efficiency photovoltaic (PV) devices, making ICT systems interesting candidates for understanding and improving PV performance.  Unfortunately, due to its absorption profile, 9,9'-bianthracene is not suitable for solar applications.  However, boron-dipyrromethenes (BODIPYs) are excellent fluorescent dyes, strongly absorbing visible light.  We describe the synthesis of symmetrical BODIPY dimers linked at the meso positions with various functionalities at the 3,5-, 2,6- and/or 1,7- positions.  The photophysical analysis of these dyads reveals solvent dependent ICT similar to that observed in 9,9'-bianthracene. Varying the substitution of the dyads positively or negatively affects the ICT and is evidenced by a change in the emission and transient absorption properties.  The properties of these dyads as thin films will also be presented.

Intramolecular charge transfer in symmetrical BODIPY dyads

243rd National Meeting (2012)

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