Tapping the near-infrared spectral region with bacteriochlorin arrays

作者: Jonathan S. Lindsey , Olga Mass , Chih-Yuan Chen

DOI: 10.1039/C0NJ00977F

关键词: BacteriochlorophyllNanotechnologyPhotomedicinePhotochemistryElectron transferAbsorption (electromagnetic radiation)ChemistryNear-infrared spectroscopyPhotosynthetic bacteriaChromophoreArtificial photosynthesis

摘要: Bacteriochlorophylls—natural pigments for absorption of near-infrared (NIR) light—underlie light-absorption and energy transduction in photosynthetic bacteria. Capturing utilizing NIR light is valuable fields ranging from artificial photosynthesis to photomedicine (photodynamic therapy, imaging, diagnostics). The desired photochemical features may be best elicited with multicomponent architectures that support efficient excited-state and/or electron transfer, yet few such arrays containing bacteriochlorins (the core chromophore bacteriochlorophylls) are known. This review outlines three synthetic approaches toward bacteriochlorins, surveys all known bacteriochlorin arrays, compares molecular design strategies light-harvesting bacteriochlorinsversus better known) porphyrins.

参考文章(36)
Michael R. Wasielewski, Ursula H. Smith, Benjamin T. Cope, Joseph J. Katz, A Synthetic Biomimetic Model of Special Pair Bacteriochlorophyll a Journal of the American Chemical Society. ,vol. 99, pp. 4172- 4173 ,(1977) , 10.1021/JA00454A054
Michael R. Wasielewski, Walter A. Svec, Synthesis of covalently linked dimeric derivatives of chlorophyll a, pyrochlorophyll a, chlorophyll b, and bacteriochlorophyll a Journal of Organic Chemistry. ,vol. 45, pp. 1969- 1974 ,(1980) , 10.1021/JO01298A043
Yihui Chen, Guolin Li, Ravindra Pandey, Synthesis of Bacteriochlorins and Their Potential Utility in Photodynamic Therapy (PDT) Current Organic Chemistry. ,vol. 8, pp. 1105- 1134 ,(2004) , 10.2174/1385272043370131
Masahiko Taniguchi, Doyoung Ra, Christine Kirmaier, Eve Hindin, Jennifer K. Schwartz, James R. Diers, Robert S. Knox, David F. Bocian, Jonathan S. Lindsey, Dewey Holten, Comparison of excited-state energy transfer in arrays of hydroporphyrins (chlorins, oxochlorins) versus porphyrins: rates, mechanisms, and design criteria. Journal of the American Chemical Society. ,vol. 125, pp. 13461- 13470 ,(2003) , 10.1021/JA035987U
Michael Krayer, Eunkyung Yang, James R. Diers, David F. Bocian, Dewey Holten, Jonathan S. Lindsey, De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls New Journal of Chemistry. ,vol. 35, pp. 587- 601 ,(2011) , 10.1039/C0NJ00771D
Tomohiro Miyatake, Hitoshi Tamiaki, Alfred R. Holzwarth, Kurt Schaffner, Artificial Light-Harvesting Antennae: Singlet Excitation Energy Transfer from Zinc Chlorin Aggregate to Bacteriochlorin in Homogeneous Hexane Solution Photochemistry and Photobiology. ,vol. 69, pp. 448- 456 ,(1999) , 10.1111/J.1751-1097.1999.TB03311.X
Jörg Dandler, Hugo Scheer, Inhibition of aggregation of [Pd]-bacteriochlorophyllides in mesoporous silica. Langmuir. ,vol. 25, pp. 11988- 11992 ,(2009) , 10.1021/LA902767X
Kei Ohkubo, Hiroshi Imahori, Jianguo Shao, Zhongping Ou, Karl M. Kadish, Yihui Chen, Gang Zheng, Ravindra K. Pandey, Mamoru Fujitsuka, Osamu Ito, Shunichi Fukuzumi, Small Reorganization Energy of Intramolecular Electron Transfer in Fullerene-Based Dyads with Short Linkage Journal of Physical Chemistry A. ,vol. 106, pp. 10991- 10998 ,(2002) , 10.1021/JP026603+
Atsuhiro Osuka, Yukihisa Wada, Kazuhiro Maruyama, Hitoshi Tamiaki, Synthesis of a Covalently Linked Bacteriopyropheophorbide --- Pyropheophorbide Hybrid Dimer Heterocycles. ,vol. 44, pp. 165- 168 ,(1997) , 10.3987/COM-95-S3