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Chiral Conjugated Corrals.
Ball, Melissa; Fowler, Brandon; Li, Panpan; Joyce, Leo A; Li, Fang; Liu, Taifeng; Paley, Daniel; Zhong, Yu; Li, Hexing; Xiao, Shengxiong; Ng, Fay; Steigerwald, Michael L; Nuckolls, Colin.
Afiliação
  • Ball M; †Department of Chemistry, Columbia University, New York, New York 10027, United States.
  • Fowler B; †Department of Chemistry, Columbia University, New York, New York 10027, United States.
  • Li P; ‡The Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Optoelectronic Nano Materials and Devices Institute, Department of Chemistry, Shanghai Normal University, Shanghai, China 200234.
  • Joyce LA; †Department of Chemistry, Columbia University, New York, New York 10027, United States.
  • Li F; §Process and Analytical Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, United States.
  • Liu T; ‡The Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Optoelectronic Nano Materials and Devices Institute, Department of Chemistry, Shanghai Normal University, Shanghai, China 200234.
  • Paley D; ‡The Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Optoelectronic Nano Materials and Devices Institute, Department of Chemistry, Shanghai Normal University, Shanghai, China 200234.
  • Zhong Y; †Department of Chemistry, Columbia University, New York, New York 10027, United States.
  • Li H; †Department of Chemistry, Columbia University, New York, New York 10027, United States.
  • Xiao S; ‡The Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Optoelectronic Nano Materials and Devices Institute, Department of Chemistry, Shanghai Normal University, Shanghai, China 200234.
  • Ng F; ‡The Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Optoelectronic Nano Materials and Devices Institute, Department of Chemistry, Shanghai Normal University, Shanghai, China 200234.
  • Steigerwald ML; †Department of Chemistry, Columbia University, New York, New York 10027, United States.
  • Nuckolls C; †Department of Chemistry, Columbia University, New York, New York 10027, United States.
J Am Chem Soc ; 137(31): 9982-7, 2015 Aug 12.
Article em En | MEDLINE | ID: mdl-26225639
We present here a new design motif for strained, conjugated macrocycles that incorporates two different aromatics into the cycle with an -A-B-A-B- pattern. In this study, we demonstrate the concept by alternating electron donors and acceptors in a conjugated cycle. The donor is a bithiophene, and the acceptor is a perylene diimide derivative. The macrocycle formed has a persistent elliptiform cavity that is lined with the sulfur atoms of the thiophenes and the π-faces of the perylene diimide. Due to the linkage of the perylene diimide subunits, the macrocycles exist in both chiral and achiral forms. We separate the three stereoisomers using chiral high-performance liquid chromatography and study their interconversion. The mechanism for interconversion involves an "intramolecular somersault" in which one of the PDIs rotates around its transverse axis, thereby moving one of its diimide heads through the plane of the cavity. These unusual macrocycles are black in color with an absorption spectrum that spans the visible range. Density functional theory calculations reveal a photoinduced electron transfer from the bithiophene to the perylene diimide.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Estresse Mecânico / Desenho de Fármacos / Compostos Macrocíclicos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2015 Tipo de documento: Article País de afiliação: Estados Unidos
Texto completo
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Estresse Mecânico / Desenho de Fármacos / Compostos Macrocíclicos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2015 Tipo de documento: Article País de afiliação: Estados Unidos