Molecular design of benzothiadiazole-based dyes for working with carbon nanotube photocatalysts

References

• Youngblood, W. J.; Lee, S.-H. A.; Maeda, K.; Mallouk, T. E. Visible Light Water Splitting Using Dye-Sensitized Oxide Semiconductors. Acc. Chem. Res. 2009, 42, 1966–1973. DOI:10.1021/ar9002398.
   PubMed Web of Science ®Google Scholar
• Chen, X.; Shen, S.; Guo, L.; Mao, S. S. Semiconductor-Based Photocatalytic Hydrogen Generation. Chem. Rev. 2010, 110, 6503–6570. DOI:10.1021/cr1001645.
   PubMed Web of Science ®Google Scholar
• Horiuchi, Y.; Toyao, T.; Takeuchi, M.; Matsuoka, M.; Anpo, M. Recent Advances in Visible-Light-Responsive Photocatalysts for Hydrogen Production and Solar Energy Conversion - from Semiconducting TiO2 to MOF/PCP Photocatalysts. Phys. Chem. Chem. Phys. 2013, 15, 13243–13253. DOI:10.1039/c3cp51427g.
   PubMed Web of Science ®Google Scholar
• Hisatomi, T.; Kubota, J.; Domen, K. Recent Advances in Semiconductors for Photocatalytic and Photoelectrochemical Water Splitting. Chem. Soc. Rev. 2014, 43, 7520–7535. DOI:10.1039/C3CS60378D.
   PubMed Web of Science ®Google Scholar
• Chen, J.; Yang, D.; Song, D.; Jiang, J.; Ma, A.; Hu, M. Z.; Ni, C. Recent Progress in Enhancing Solar-to-Hydrogen Efficiency. J. Power Sources 2015, 280, 649–666. DOI:10.1016/j.jpowsour.2015.01.073.
   Web of Science ®Google Scholar
• Wang, X.; Maeda, K.; Thomas, A.; Takanabe, K.; Xin, G.; Carlsson, J. M.; Domen, K.; Antonietti, M. A. Metal-Free Polymeric Photocatalyst for Hydrogen Production from Water under Visible Light. Nat. Mater. 2009, 8, 76–80. DOI:10.1038/nmat2317.
   PubMed Web of Science ®Google Scholar
• Takanabe, K.; Kamata, K.; Wang, X.; Antonietti, M.; Kubota, J.; Domen, K. Photocatalytic Hydrogen Evolution on Dye-Sensitized Mesoporous Carbon Nitride Photocatalyst with Magnesium Phthalocyanine. Phys. Chem. Chem. Phys. 2010, 12, 13020–13025. DOI:10.1039/c0cp00611d.
   PubMed Web of Science ®Google Scholar
• Zhang, X.; Yu, L.; Zhuang, C.; Peng, T.; Li, R.; Li, X. Highly Asymmetric Phthalocyanine as a Sensitizer of Graphitic Carbon Nitride for Extremely Efficient Photocatalytic H2 Production under near-Infrared Light. ACS Catal. 2014, 4, 162–170. DOI:10.1021/cs400863c.
   Web of Science ®Google Scholar
• Kataura, H.; Kumazawa, Y.; Maniwa, Y.; Umezu, I.; Suzuki, S.; Ohtsuka, Y.; Achiba, Y. Optical Properties of Single-Wall Carbon Nanotubes. Synth. Met. 1999, 103, 2555–2558. DOI:10.1016/S0379-6779(98)00278-1.
   Web of Science ®Google Scholar
• Weisman, R. B.; Bachilo, S. M. Dependence of Optical Transition Energies on Structure for Single-Walled Carbon Nanotubes in Aqueous Suspension: An Empirical Kataura Plot. Nano Lett. 2003, 3, 1235–1238. DOI:10.1021/nl034428i.
   Web of Science ®Google Scholar
• Liu, H.; Nishide, D.; Tanaka, T.; Kataura, H. Large-Scale Single-Chirality Separation of Single-Wall Carbon Nanotubes by Simple Gel Chromatography. Nat. Commun. 2011, 2, 309. [Database] DOI:10.1038/ncomms1313.
   PubMed Web of Science ®Google Scholar
• Ihly, R.; Mistry, K. S.; Ferguson, A. J.; Clikeman, T. T.; Larson, B. W.; Reid, O.; Boltalina, O. V.; Strauss, S. H.; Rumbles, G.; Blackburn, J. L. Tuning the Driving Force for Exciton Dissociation in Single-Walled Carbon Nanotube Heterojunctions. Nat. Chem. 2016, 8, 603–609. DOI:10.1038/nchem.2496.
   PubMed Web of Science ®Google Scholar
• Blackburn, J. L. Semiconducting Single-Walled Carbon Nanotubes in Solar Energy Harvesting. ACS Energy Lett. 2017, 2, 1598–1613. DOI:10.1021/acsenergylett.7b00228.
   Web of Science ®Google Scholar
• Shea, M. J.; Wang, J.; Flach, J. T.; Zanni, M. T.; Arnold, M. S. Less Severe Processing Improves Carbon Nanotube Photovoltaic Performance. APL Mater. 2018, 6, 056104. DOI:10.1063/1.5026853.
   Web of Science ®Google Scholar
• Pfohl, M.; Glaser, K.; Graf, A.; Mertens, A.; Tune, D. D.; Puerckhauer, T.; Alam, A.; Wei, L.; Chen, Y.; Zaumseil, J.; et al. Probing the Diameter Limit of Single Walled Carbon Nanotubes in SWCNT: Fullerene Solar Cells. Adv. Energy Mater. 2016, 6, 1600890. DOI:10.1002/aenm.201600890.
   Web of Science ®Google Scholar
• Takaguchi, Y.; Tamura, M.; Sako, Y.; Yanagimoto, Y.; Tsuboi, S.; Uchida, T.; Shimamura, K.; Kimura, S.; Wakahara, T.; Maeda, Y.; et. al. Fullerodendron-Assisted Dispersion of Single-Walled Carbon Nanotubes via Noncovalent Functionalization. Chem. Lett. 2005, 34, 1608–1609. 2005). DOI:10.1246/cl.2005.1608.
   Web of Science ®Google Scholar
• Sandanayaka, A. S. D.; Takaguchi, Y.; Sako, Y.; Tamura, M.; Ito, O. Photoinduced Electron Transfer of Single Walled Carbon Nanotubes Surrounded by Fullerodendrimers in Aqueous Media. Adv. Sci. Lett. 2010, 3, 1–5. DOI:10.1166/asl.2010.1166.
   Google Scholar
• Suzuki, H.; Iizumi, Y.; Tange, M.; Joung, S.-K.; Furube, A.; Wada, T.; Tajima, T.; Takaguchi, Y.; Okazaki, T. Spectroscopic Characterization of Nanohybrids Consisting of Single-Walled Carbon Nanotubes and Fullerodendron. Fullerenes Nanotubes Carbon Nanostruct. 2014, 22, 75–87. DOI:10.1080/1536383X.2013.794340.
   Web of Science ®Google Scholar
• Tajima, T.; Sakata, W.; Wada, T.; Tsutsui, A.; Nishimoto, S.; Miyake, M.; Takaguchi, Y. Photosensitized Hydrogen Evolution from Water Using a Single-Walled Carbon Nanotube/Fullerodendron/SiO2 Coaxial Nanohybrid. Adv. Mater. 2011, 23, 5750–5754. DOI:10.1002/adma.201103472.
   PubMed Web of Science ®Google Scholar
• Kurniawan, K.; Tajima, T.; Kubo, Y.; Miyake, H.; Kurashige, W.; Negishi, Y.; Takaguchi, Y. Incorporating a TiOx Shell in Single-Walled Carbon Nanotube/Fullerodendron Coaxial Nanowires: Increasing the Photocatalytic Evolution of H2 from Water under Irradiation with Visible Light. RSC Adv. 2017, 7, 31767–31770. DOI:10.1039/C7RA05412B.
   Web of Science ®Google Scholar
• Sasada, Y.; Tajima, T.; Wada, T.; Uchida, T.; Nishi, M.; Ohkubo, T.; Takaguchi, Y. Photosensitized Hydrogen Evolution from Water Using Single-Walled Carbon Nanotube/Fullerodendron/Pt(II) Coaxial Nanohybrids. New J. Chem. 2013, 37, 4214–4219. DOI:10.1039/c3nj00790a.
   Web of Science ®Google Scholar
• Murakami, N.; Tango, Y.; Miyake, H.; Tajima, T.; Nishina, Y.; Kurashige, W.; Negishi, Y.; Takaguchi, Y. SWCNT Photocatalyst for Hydrogen Production from Water upon Photoexcitation of (8, 3) SWCNT at 680-nm Light. Sci. Rep. 2017, 7, 43445. DOI:10.1038/srep43445.
   PubMed Web of Science ®Google Scholar
• Kurniawan, K.; Murakami, N.; Tango, Y.; Izawa, T.; Nishikawa, K.; Watanabe, K.; Miyake, H.; Tajima, T.; Takaguchi, Y. H2-Evolving SWCNT Photocatalyst for Effective Use of Solar Energy. Proc. Nat. Res. Soc. 2017, 1, 01004. DOI:10.11605/j.pnrs.201701004.
   Google Scholar
• Yanagi, K.; Iakoubovskii, K.; Kazaoui, S.; Minami, N.; Ma-Niwa, Y.; Miyata, Y.; H, K. Light-Harvesting Function of β-Carotene Inside Carbon Nanotubes. Phys. Rev. B 2006, 74, 155420. DOI:10.1103/PhysRevB.74.155420.
   Web of Science ®Google Scholar
• Yanagi, K.; Iakoubovskii, K.; Matsui, H.; Matsuzaki, H.; Okamoto, H.; Miyata, Y.; Maniwa, Y.; Kazaoui, S.; Minami, N.; Kataura, H. Photosensitive Function of Encapsulated Dye in Carbon Nanotubes. J. Am. Chem. Soc. 2007, 129, 4992–4997. DOI:10.1021/ja067351j.
   PubMed Web of Science ®Google Scholar
• Loi, M. A.; Gao, J.; Cordella, F.; Blondeau, P.; Menna, E.; Bartova, B.; Hebert, C.; Lazar, S.; Botton, G. A.; Milko, M.; Ambrosch-Draxl, C. Encapsulation of Conjugated Oligomers in Single-Walled Carbon Nanotubes: Towards Nanohybrids for Photonic Devices. Adv. Mater. 2010, 22, 1635–1639. DOI:10.1002/adma.200903527.
   PubMed Web of Science ®Google Scholar
• Okazaki, T.; Izumi, Y.; Okubo, S.; Kataura, H.; Liu, Z.; Suenaga, K.; Tahara, Y.; Yudasaka, M.; Okada, S.; Iijima, S. Coaxially Stacked Coronene Columns inside Single-Walled Carbon Nanotubes. Angew. Chem. Int. Ed. 2011, 50, 4853–4857. DOI:10.1002/anie.201007832.
   PubMed Web of Science ®Google Scholar
• Bezouw, S.; Arias, D.; Ihly, R.; Cambré, S.; Gerguson, A.; Campo, J.; Johnson, J. C.; Defillet, J.; Wenseleers, W.; Blackburn, J. L. Excitation Energy Transfer from Encapsulated Dye Molecules toward Single-Walled Carbon Nanotubes. ACS Nano. 2018, 12, 6881–6894. DOI:10.1021/acsnano.8b02213.
   PubMed Web of Science ®Google Scholar
• Miyake, H.; Tajima, T.; Takaguchi, Y. Thiophene Derivatives Bearing Ferrocenylthiocarbonyl Groups. Chem. Lett. 2017, 46, 48–50. DOI:10.1246/cl.160866.
   Web of Science ®Google Scholar
• Murakami, N.; Miyake, H.; Tajima, T.; Nishikawa, K.; Hirayama, R.; Takaguchi, Y. Enhanced Photosensitized Hydrogen Production by Encapsulation of Ferrocenyl Dyes into Single-Walled Carbon Nanotubes. J. Am. Chem. Soc. 2018, 140, 3821–3824. DOI:10.1021/jacs.7b12845.
   PubMed Web of Science ®Google Scholar