The heavy-atom effect on xanthene dyes for photopolymerization by visible light

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We investigated the influence of heavy halogen atoms (Br and I) on xanthene dyes for polymerization based on visible-light photoredox initiation. Since the heavy atoms directly affect intersystem crossing (ISC), which can act as a gatekeeper in the photoredox cycle and which was expected to also affect intermolecular photoinduced electron transfer (PET), we attempted to quantify the influence of the halogens. Six different xanthene dyes were chosen based on the number and types of heavy atoms on the xanthene ring. Thus, the photopolymerization degree clearly increased in the following order: fluorescein < 4',5'-dibromofluorescein <= 2',4',5',7'-tetrabromofluorescein < 2',4',5',7'-tetraiodofluorescein. Furthermore, 4',5'-dibromorhodamine 6G showed a drastic enhancement in the photopolymerization degree, compared with rhodamine 6G. Therefore, we concluded that the presence of halogens on the xanthene ring increases the photoredox initiating performance due to the enhanced ISC efficiency and PET rate.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2019-11
Language
English
Article Type
Article
Citation

POLYMER CHEMISTRY, v.10, no.42, pp.5737 - 5742

ISSN
1759-9954
DOI
10.1039/c9py01252d
URI
http://hdl.handle.net/10203/268835
Appears in Collection
NT-Journal Papers(저널논문)
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