For some time our group has been focused on the design and synthesis of derivatives of boron subphthalocyanine (BsubPc) for application in organic electronics with a specific focus on organic photovoltaics and light emitting diodes. In most cases, organic electronic devices utilize the prototypical BsubPc, chloro boron subphthalocyanine (Cl-BsubPc). We have shown that by using facile chemical transformations we can tailor the nature of the BsubPc to a dye, sublimate, engineered crystal or polymer. Early on in our research program we showed that peripheral functionalization of the BsubPc moiety had detrimental effects on the electrochemical behaviour/stability. We therefore focused on chemical derivatization of the boron metal centre while maintaining the hydrogen periphery. The chemical transformations we have found most successfully rely on the oxo-philicity of the boron metal centre. Transformations include phenoxylation and acetylation.
In this presentation I will outline examples of each type of BsubPcs, the chemistry we have used to achieve each derivative, in addition to presenting their application in organic electronic devices including organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs).
We have also recently been exploring the chemistry of boron subnaphthalocyanines (BsubNcs). I will outline both our synthetic results and the application of BsubNcs in OPVs.
Finally, I will also highlight our group’s recent exploration of other p-block metal phthalocyanines (M-Pcs) including Pcs of aluminum, silicon, germanium and phosphorous. In each case the metal was chosen due to its abundance and its ability to participate in our previously established oxo-philic based chemistry. From this group silicon phthalocyanine has emerged as an electron transporting material shown to function in a fullerene free OPV. We have also shown that phenoxylation enhances the performance of silicon phthalocyanine as an electron transporting material.
Coauthors will be cited as appropriate throughout the presentation.
Leading References: (1) “Assessing the potential roles of silicon and germanium phthalocyanines in planar heterojunction organic photovoltaic devices and how pentafluoro phenoxylation can enhance p-p interactions and device performance” Lessard, B.H.; et al. ACS Appl. Mat. Inter., 2015, just accepted, 10.1021/am508491v. (2) “Pentafluorophenoxy Boron Subphthalocyanine (F5BsubPc) as a Multifunctional Material for Organic Photovoltaics.” Morse, G.E.; et al. ACS Appl. Mat. Inter., 2014, 6 (3), 1515–1524. (3) “Utilizing the π-Acidity of Boron Subphthalocyanine to Achieve Novel Solid-State Arrangements.” Paton, A.S.; et al. Crystal Growth & Des., 2013, 13 (12), 5368–5374. (4) “Halogen bonds can direct the solid state arrangement of phenoxy-boron subphthalocyanines.” Virdo, J.D.; et al. CrystEngComm, 2013, 15, 3187-3199. (5) “Boron Subphthalocyanines as Organic Electronic Materials” Morse, G.E.; Bender, T.P.; Appl. Mater. Inter., 2012, 4(10), 5055–5068.