Synthesis and photoisomerization of fullerene- and oligo(phenylene ethynylene)-azobenzene derivatives. 2008

Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
Department of Chemistry, Smalley Institute for Nanoscale Science and Technology, Rice University, MS-222, 6100 Main Street, Houston, Texas 77005, USA.

The presence of fullerenes and oligo(phenylene ethynylene)s (OPEs) in azobenzene derivatives have a large effect on the photoisomerization behavior of the molecules. Fullerenes reduce the photoisomerization yield for cis isomers, and the OPEs, when directly attached to the azobenzenes, have a similar yet smaller effect when compared with the fullerenes. While these effects have not been previously considered for fullerene--and OPE-azobenzene derivatives, they were clearly detected in our work using NMR and UV-vis spectroscopy methods. The intramolecular electronic energy transfer between the fullerene and azobenzene moiety was examined in two cases in which separation of the two functional groups was small, as in 1, or large, as in 2. Almost no photoisomerization was observed for 1, while significant photoisomerization was observed for 2, apparently due to the effective isolation and blocking of electronic communication between the two functional groups.

UI MeSH Term Description Entries

Related Publications

Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
January 2007, Angewandte Chemie (International ed. in English),
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
July 2020, Nanoscale,
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
November 2011, Chemistry (Weinheim an der Bergstrasse, Germany),
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
February 2007, Organic letters,
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
August 2013, Chemistry, an Asian journal,
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
June 2006, Chemistry (Weinheim an der Bergstrasse, Germany),
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
November 2005, Nano letters,
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
May 2020, ACS applied materials & interfaces,
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
July 2002, Journal of the American Chemical Society,
Yasuhiro Shirai, and Takashi Sasaki, and Jason M Guerrero, and Byung-Chan Yu, and Phillip Hodge, and James M Tour
September 2022, Nanoscale horizons,
Copied contents to your clipboard!