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Alternatively, methyl 13<jats:sup>1<\/jats:sup>\u2010cyanomethylene\u2010pyropheophorbides were produced by Wittig reactions of 13<jats:sup>1<\/jats:sup>\u2010oxo\u2010chlorins with Ph<jats:sub>3<\/jats:sub>P=<jats:styled-content style=\"fixed-case\">CHCN<\/jats:styled-content>. Self\u2010aggregation of zinc complexes of the semi\u2010synthetic chlorophyll derivatives possessing a hydroxy or methoxy group at the 3<jats:sup>1<\/jats:sup>\u2010position was examined in 1%(v\/v) tetrahydrofuran or dichloromethane and hexane by electronic absorption and circular dichroism spectroscopy. Although intermolecular hydrogen\u2010bonding between the 3<jats:sup>1<\/jats:sup>\u2010hydroxy and 13<jats:sup>1<\/jats:sup>\u2010oxo groups of bacteriochlorophylls\u2010<jats:italic>c<\/jats:italic>\/<jats:italic>d<\/jats:italic>\/<jats:italic>e<\/jats:italic>\/<jats:italic>f<\/jats:italic> was essential for their self\u2010aggregation in natural light\u2010harvesting antenna systems (=chlorosomes), zinc 3<jats:sup>1<\/jats:sup>\u2010hydroxy\u201013<jats:sup>1<\/jats:sup>\u2010di\/monocyanomethylene\u2010chlorins self\u2010aggregated in the less\/lesser polar organic solvents to form chlorosome\u2010like large oligomers in spite of lacking the 13<jats:sup>1<\/jats:sup>\u2010oxo moiety as the hydrogen\u2010bonding acceptor. Zinc 3<jats:sup>1<\/jats:sup>\u2010methoxy\u201013<jats:sup>1<\/jats:sup>\u2010dicyanomethylene\u2010chlorin gave similar self\u2010aggregates regardless of lack of both the 3<jats:sup>1<\/jats:sup>\u2010hydroxy and 13<jats:sup>1<\/jats:sup>\u2010oxo groups. The present self\u2010aggregation was ascribable to stronger coordination of the 3<jats:sup>1<\/jats:sup>\u2010oxygen atom to the central zinc than the conventional systems, where the electron\u2010withdrawing cyano group(s) increased the coordinative ability of the central zinc through the chlorin <jats:italic>\u03c0<\/jats:italic>\u2010system.<\/jats:p>","DOI":"10.1111\/php.12327","type":"journal-article","created":{"date-parts":[[2014,8,6]],"date-time":"2014-08-06T15:53:29Z","timestamp":1407340409000},"page":"1277-1286","source":"Crossref","is-referenced-by-count":10,"title":["Self\u2010aggregation of Synthetic Zinc Chlorophyll Derivatives Possessing 3<sup>1<\/sup>\u2010Hydroxy or Methoxy Group and 13<sup>1<\/sup>\u2010Mono\u2010 or Dicyanomethylene Moiety in Nonpolar Organic Solvents as Models of Chlorosomal Bacteriochlorophyll\u2010<i>d<\/i> Aggregates"],"prefix":"10.1111","volume":"90","author":[{"given":"Hitoshi","family":"Tamiaki","sequence":"first","affiliation":[{"name":"Graduate School of Life Sciences Ritsumeikan University Kusatsu Shiga Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masaki","family":"Kuno","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences Ritsumeikan University Kusatsu Shiga Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masaki","family":"Ohata","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences Ritsumeikan University Kusatsu Shiga Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,9]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/181662a0"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/176325a0"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/318618a0"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1562\/2006-02-27-IR-819"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1142\/9789814322386_0003"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.06.016"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbabio.2009.05.010"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2009.12.027"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11120-013-9869-3"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3pp50253h"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02184165"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.09.007"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.06.046"},{"key":"e_1_2_6_15_1","first-page":"45","volume-title":"Handbook of Porphyrin Science","author":"Gunderson V. 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