Computational Modeling of Boron Subphthalocyanines and Subnaphthalocyanines to Justify Their Development and to Predict and Confirm Their Electrochemical and Physical Properties

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For some time, our group has been focused on the molecular design, synthesis and application of derivatives of boron subphthalocyanines (BsubPcs) and subnaphthalocyanines (BsubNcs), which are macrocyclic molecules with a chelated central boron atom. Our focal point has been and continues to be equally balanced between the basic and applied chemistry of BsubPcs/BsubNcs and their application as light absorbing and electronic conducting materials in organic photovoltaics (OPVs)/organic solar cells. Electrochemical properties being critical to this application. For OPVs, we selected a preferred approach to the development of BsubPcs/BsubNcs whereby their molecular design and their synthesis is justified through a development cycle which includes data accumulation of their basic physical chemistry properties, their immediate integration into OPVs and their stability evaluation when applied into OPVs/organic solar cells. Based on data acquisition, we then cycle back to consider alternative molecular designs of BsubPcs/BsubNcs. Recently we have re-Integrated into this cycle our computational modeling methodology which is used to screen potential BsubPcs/BsubNcs for their application in OPVs/organic solar cells and other organic electronic devices.For this presentation I will begin by outlining how we have re-adopted our past computational model to help develop these materials. I will start by showing how we calibrate several levels of computational modeling relative to firm experimental data. I will highlight how a low level and high level computational model can be calibrated and the difference between them. I will then move onto several examples of how we have developed BsubPcs/BsubNcs for application in OPVs and other organic electronic devices utilizing this method.An example I will show is that we have recently identified a pathway to BsubPcs whereby all carbons are bio-sourced. In order to justify their synthesis with the desired OPV application, I will highlight how the computational model justified the time and resource commitment to their synthesis and development. I will also show how the computational calibration model did accurately predict their relevant properties, the prediction being a level of justification for their development.I will outline several other BsubPc/BsubNc macrocycle structures that where either justified by the computational model to be developed or where not justified. I will also highlight to the community progress in avoiding bay-position halogenation of the BsubNc macrocycles during their formation.Additional co-authors/investigators will be identified during this presentation. Figure 1