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9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units : A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units : A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior |
"/Ishigaki, Yusuke/"Ishigaki, Yusuke ,
"/Hayashi, Yuki/"Hayashi, Yuki ,
"/Sugawara, Kazuma/"Sugawara, Kazuma ,
"/Shimajiri, Takuya/"Shimajiri, Takuya ,
"/Nojo, Wataru/"Nojo, Wataru ,
"/Katoono, Ryo/"Katoono, Ryo ,
"/Suzuki, Takanori/"Suzuki, Takanori
22
(
11
)
, p.1900 , 2017-11 , MDPI
ISSN:1420-3049
Description
The title dispiro hydrocarbon 1 was designed as a new electrochromic material. This multiply clamped hexaphenylethane-type electron donor was prepared from 2,2'-diiodobiphenyl via biphenyl-2,2'-diylbis(dibenzotropylium) 2(2+) salt. X-ray analysis of 1 revealed a highly strained structure as reflected by an elongated ethane bond [bond length: 1.6665(17) angstrom] and nearly eclipsed conformation. The weakened bond was cleaved upon two-electron oxidation to regenerate the deeply colored dication 2(2+). The reversible interconversion between 1 and 2(2+) is accompanied not only by a drastic color change but also by C-C bond formation/cleavage. Thus, the voltammogram showed a pair of well-separated redox waves, which is characteristic of "dynamic redox (dyrex)" behavior. The tetrahydro derivative of 1 with two units of spiro(dibenzocycloheptadiene), which suffers from more severe steric congestion, was also prepared. The crystallographically determined bond length for the central C-C bond [1.705(4) angstrom] is greatest among the values reported for 9,9,10,10-tetraaryl-9,10-dihydrophenanthrene derivatives.
Full-Text
https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/68293/3/Molecules22-11%201900.pdf
https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/68293/2/Supplementary%20materials.pdf
