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Rates of Ring Opening of Radical Cation Intermediates Govern Differences in Thermoluminescence between 1‐ and 2‐Naphthyl‐Substituted Methylenecyclopropanes.
- Source :
-
ChemPhotoChem . Mar2020, Vol. 4 Issue 3, p168-172. 5p. - Publication Year :
- 2020
-
Abstract
- In this study, we observed that methylenecyclopropane 1 c, possessing geminal phenyl and 1‐naphthyl groups at C‐2 of the three membered ring, emits green thermoluminescence (TL) in a low temperature matrix, associated with two sets of bands in the 480–600 and 600–700 nm regions. The bands are assigned to phosphorescence from 31 c* and triplet‐triplet (T−T) fluorescence (FL) from the corresponding trimethylenemethane biradical 32 c..*, respectively. In contrast, as previously reported, the analogous 2‐naphthyl derivative 1 b emits red TL associated with two bands in the 350–450 and 600–700 nm regions, which are assigned to FL from 11 b* and T−T FL from 32 b..*. The results of spectroscopic studies and density functional theory calculations show that the observed dissimilarity in the TL properties of 1 b and 1 c is a consequence of differences in the rate of methylenecyclopropane ring opening of 1 b.+ and 1 c.+ associated with stereoelectronic effects of the naphthyl groups. [ABSTRACT FROM AUTHOR]
- Subjects :
- *RADICAL cations
*DENSITY functional theory
*PHENYL group
*THERMOLUMINESCENCE
Subjects
Details
- Language :
- English
- ISSN :
- 23670932
- Volume :
- 4
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- ChemPhotoChem
- Publication Type :
- Academic Journal
- Accession number :
- 142267562
- Full Text :
- https://doi.org/10.1002/cptc.201900230