Thermal Conversion Behavior and Morphology Control of Benzoporphycene from a Novel Soluble Precursor

Saeki, Hiroyuki; Kurimoto, Omi; Misaki, Masahiro; Kuzuhara, Daiki; Yamada, Hiroko; Ueda, Y.

doi:10.7567/apex.6.035601

Cited by 17 publications

(10 citation statements)

References 21 publications

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“…Tetrabenzoporphycene 35 was used as a p-type semiconductor for organic solar cells. [57][58][59] Dodeca-substituted porphycenes 45 were prepared by McMurry coupling of the diacylated BCOD-dipyrroles 44 (Scheme 15). 60 The single-crystal structure of 45b showed a ruffled shape for the BCOD-porphycene.…”

Section: Scheme 13 Synthesis Of Tetraarylporphycenesmentioning

confidence: 99%

Porphyrinoids with Vinylene Bridges

Kuzuhara

Yamada

2020

Synlett

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Porphyrinoids containing vinylene bridges, such as triphyrin(2.1.1), porphycene, porphyrin(2.1.2.1), and hexaphyrin(2.1.2.1.2.1), are a relatively new family of porphyrinoids. Vinylene bridges give porphyrinoids a lower symmetry and a flexibility of the framework and they permit cis/trans-isomerization reactions; these factors confer unique properties to these substances, such as coordination to metal ions and aromaticity switching. In this account, the synthesis, crystal structures, and properties of new porphyrinoids containing vinylene bridges are summarized.1 Introduction2 Triphyrin(2.1.1)3 Porphycene4 Porphyrin(2.1.2.1)5 Hexaphyrin(2.1.2.1.2.1)6 Conclusion

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Section: Scheme 13 Synthesis Of Tetraarylporphycenesmentioning

confidence: 99%

Porphyrinoids with Vinylene Bridges

Kuzuhara

Yamada

2020

Synlett

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“…We have previously reported on tetrabenzo-porphycene (β-TBPc, Figure 1 ) [ 13 ] and tetranaphthoporphycene (β-TNPc) [ 14 ], which demonstrated red-shifted absorption from pristine Pc with an increasing number of benzene rings. Organic solar cells (OSC) based on β-TBPc as a p-type material and PC 61 BM as an n-type material exhibited 1.54% power-conversion efficiency [ 15 , 16 , 17 ]. Sessler and Panda independently reported dinaphthoporphycenes (DNPcs), in which absorptions reached around 800 nm [ 8 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes

et al. 2017

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9,10-Quinoxaline-fused porphycenes 1a-H2 and 1b-H2 were synthesized by intramolecular McMurry coupling. As a result of the annulation of the quinoxaline moiety on the porphycene skeleton, 1a-H2 and 1b-H2 display absorption and fluorescence in the near infra-red (NIR) region. Additionally, the quinoxaline moieties of 1a-H2 and 1b-H2 act as electron-withdrawing groups, introducing lower reduction potentials than for pristine porphycene. The protonation occurred at the nitrogen atoms in the cavity of freebase porphycenes and at the quinoxaline moieties for their nickel complexes to give diprotonic species.

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“…The precursor approach provides nonconventional means toward the achievement of effective active-layer structures through solution-based deposition processes. − In this approach, a well-soluble and nonaggregating precursor compound is solution-deposited on a substrate and then quantitatively converted in situ to a semiconducting material by an external stimulus such as heat or light. In pioneering work, Matsuo, Nakamura, and co-workers successfully demonstrated that photovoltaic active layers with highly ordered interpenetrating domains could be solution-processed by employing carefully optimized deposition conditions in the thermoprecursor approach where tetrabenzoporphyrin and bis(dimethylphenylsilylmethyl)[60]fullerene (SIMEF) were used as p- and n-type materials, respectively .…”

Section: Introductionmentioning

confidence: 99%

Photoprecursor Approach Enables Preparation of Well-Performing Bulk-Heterojunction Layers Comprising a Highly Aggregating Molecular Semiconductor

Suzuki

Yamaguchi

Takahashi

et al. 2016

ACS Appl. Mater. Interfaces

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Active-layer morphology critically affects the performance of organic photovoltaic cells, and thus its optimization is a key toward the achievement of high-efficiency devices. However, the optimization of active-layer morphology is sometimes challenging because of the intrinsic properties of materials such as strong self-aggregating nature or low miscibility. This study postulates that the "photoprecursor approach" can serve as an effective means to prepare well-performing bulk-heterojunction (BHJ) layers containing highly aggregating molecular semiconductors. In the photoprecursor approach, a photoreactive precursor compound is solution-deposited and then converted in situ to a semiconducting material. This study employs 2,6-di(2-thienyl)anthracene (DTA) and [6,6]-phenyl-C71-butyric acid methyl ester as p- and n-type materials, respectively, in which DTA is generated by the photoprecursor approach from the corresponding α-diketone-type derivative DTADK. When only chloroform is used as a cast solvent, the photovoltaic performance of the resulting BHJ films is severely limited because of unfavorable film morphology. The addition of a high-boiling-point cosolvent, o-dichlorobenzene (o-DCB), to the cast solution leads to significant improvement such that the resulting active layers afford up to approximately 5 times higher power conversion efficiencies. The film structure is investigated by two-dimensional grazing-incident wide-angle X-ray diffraction, atomic force microscopy, and fluorescence microspectroscopy to demonstrate that the use of o-DCB leads to improvement in film crystallinity and increase in charge-carrier generation efficiency. The change in film structure is assumed to originate from dynamic molecular motion enabled by the existence of solvent during the in situ photoreaction. The unique features of the photoprecursor approach will be beneficial in extending the material and processing scopes for the development of organic thin-film devices.

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Thermal Conversion Behavior and Morphology Control of Benzoporphycene from a Novel Soluble Precursor

Cited by 17 publications

References 21 publications

Porphyrinoids with Vinylene Bridges

Porphyrinoids with Vinylene Bridges

Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes

Photoprecursor Approach Enables Preparation of Well-Performing Bulk-Heterojunction Layers Comprising a Highly Aggregating Molecular Semiconductor

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