Unusually Long-Wavelength Emissions of Cyclopropanes: New Insight into C−C Bond Homolysis

Manabu Abe, Kousei Kanahara, Norito Kadowaki, Chun Jui Tan, Hui Hsu Gavin Tsai

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Bond homolysis (BHo) is a fundamental concept in chemical-bonding phenomena. To date, research studies on the BHo concept have provided crucial information for understanding the nature of chemical bonding and reactions. Two potential-energy minima, a σ-bonding isomer and a singlet-diradical isomer, have been known to exist in carbon–carbon BHo. Herein, a third isomer, that is, a puckered singlet diradical exhibiting unstructured long-wavelength fluorescence beyond 460 nm, was first observed in the excited states of 1,4-diarylbicyclo[2.1.0]pentane derivatives. The careful selection of appropriate substituents in the bicyclic structures enabled direct spectral detection. State-of-the-art ab initio quantum chemical calculations quantitatively reproduced the experimental observations. This new finding provides new insight into carbon–carbon bond-breaking and -forming processes.

Original languageEnglish
Pages (from-to)7595-7600
Number of pages6
JournalChemistry - A European Journal
Volume24
Issue number30
DOIs
StatePublished - 28 May 2018

Keywords

  • bond homolysis
  • cyclopropane
  • puckered structures
  • radicals

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