期刊
JOURNAL OF MATERIALS CHEMISTRY A
卷 4, 期 24, 页码 9566-9577出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ta02457b
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Chloro-boron subnaphthalocyanine (Cl-BsubNc) has recently attracted significant interest as a light-harvesting and charge transporting material in organic photovoltaic devices (OPVs) by enabling an 8.4% efficient planar heterojunction OPV cell. We present herein a variety of experimental data that supports the conclusion that Cl-BsubNc, whether synthesized via literature methods or our in-house methods or purchased commercially, is actually a mixed alloyed composition of Cl-BsubNcs with random amounts of chlorination at the bay position(s) of the BsubNc macrocyclic structure which we hereafter will refer to as Cl-Cl(n)BsubNc(s). We outline our efforts to develop alternative chemical processes, whereby we did obtain samples with lower and higher amounts of bay position chlorination. However, we were unable to obtain a pure, non-bay chlorinated sample of Cl-BsubNc. The positions and frequencies of the peripheral chlorine atoms were determined via single crystal X-ray crystallography of two different mixed alloyed compositions of Cl-Cl(n)BsubNc samples and MS and XPS analysis of all Cl-Cl(n)BsubNc samples. The photo-and electro-physical properties were found to differ amongst the Cl-Cl(n)BsubNc samples with varying amounts of chlorination. These differences also translated into varying performance within planar heterojunction OPVs, whereby a mixture of Cl-Cl(n)BsubNcs with lower amounts of chlorination produced less efficient OPVs (albeit with a higher open circuit voltage) compared to a mixture with higher amounts of chlorination. Additionally, an in-house made sample of Cl-Cl(n)BsubNc, with the highest level of bay position chlorination, yielded the best performing OPVs through an improved fill factor. A commercial sample of Cl-Cl(n)BsubNc also yielded OPVs with efficiencies equivalent to a Cl-Cl(n)BsubNc sample prepared in our laboratory. This mixture of Cl-Cl(n)BsubNcs is therefore likely to be present in the reported 8.4% efficient OPV device. Our results therefore offer a cautionary note that the Cl-BsubNc samples used within the existing literature are likely not a pure chemical composition but are rather mixtures of Cl-Cl(n)BsubNcs with bay position chlorination. Our findings clarify the previous literature results on the chemistry of Cl-BsubNc, firm up the photo-and electro-physical properties of these materials, and offer additional insight into their application as functional materials in efficient OPVs.
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