AI Article Synopsis
- The compound dispiro hydrocarbon 1 is a novel electrochromic material derived from 2,2'-diiodobiphenyl, exhibiting a strained structure with an elongated bond that influences its properties.
- Upon oxidation, the weakened bond in 1 undergoes cleavage, leading to a colored dication 2, and the transition between these states is marked by significant color changes and bond dynamics.
- A tetrahydro variant of 1 shows increased steric hindrance and features the largest central carbon-carbon bond length recorded for similar compounds, indicating unique structural characteristics.
Article Abstract
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 salt. X-ray analysis of 1 revealed a highly strained structure as reflected by an elongated "ethane" bond [bond length: 1.6665(17) Å] and nearly eclipsed conformation. The weakened bond was cleaved upon two-electron oxidation to regenerate the deeply colored dication 2. The reversible interconversion between 1 and 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) Å] is greatest among the values reported for 9,9,10,10-tetraaryl-9,10-dihydrophenanthrene derivatives.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150351 | PMC |
| http://dx.doi.org/10.3390/molecules22111900 | DOI Listing |
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