Exploiting visible-light induced radical to cation transformation pathway for reactivity enhanced electrophilic aromatic substitution polymerization of heteroaromatics
Authors:
- Emirhan Gencosman,
- Huseyin Cem Kiliclar,
- Pawel Fiedor,
- Gorkem Yilmaz,
- Joanna Ortyl,
- Yusuf Yagci,
- Baris Kiskan
Abstract
A straightforward approach is employed to synthesize methylene-bridged poly(hetero aromatic)s based on furan, pyrrole, thiophene, and thiophene derivatives. The process involves an electrophilic aromatic substitution reaction facilitated by a visible light-initiated system consisting of manganese decacarbonyl and an iodonium salt. The approach mainly relies on the formation of halomethylium cation, the attack of this cation to heteroaromatic, regeneration of methylium cation on the heteroaromatic, and reactivity differences between halomethylium and heteroaromatic methylium cations for successful polymerizations. This innovative synthetic strategy lead to the formation of polymers with relatively high molecular weights as the stoichiometric imbalance between the comonomers increased. Accordingly, these newly obtained polymers exhibit remarkable fluorescence properties, even at excitation wavelengths as low as 330 nm. Moreover, by harnessing the halogens at chain ends of homopolymers, block copolymers are successfully synthesized, offering opportunities for tailored applications in diverse fields. © 2023 Wiley-VCH GmbH.
- Record ID
- CUTf29af420ec4b48d6a551b45d78d62e62
- In press
- Yes
- Publication categories
- ;
- Author
- Journal series
- Macromolecular Rapid Communications, ISSN 1022-1336, e-ISSN 1521-3927
- Issue year
- 2023
- Pages
- [1-7]
- Article number
- 2300458
- Other elements of collation
- rys.; schem.; tab.; wykr.; Bibliografia (na s.) - 6-7; Bibliografia (liczba pozycji) - 50; Oznaczenie streszczenia - Streszcz. ang.; Numeracja w czasopiśmie - Article in press
- Keywords in English
- electrophilic aromatic substitution, manganese decacarbonyl, onium salt, photochemistry, visible light-induced polymerization
- ASJC Classification
- ; ;
- DOI
- DOI:10.1002/marc.202300458 Opening in a new tab
- URL
- https://onlinelibrary.wiley.com/doi/full/10.1002/marc.202300458 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 100
- Score source
- journalList
- Score
- Publication indicators
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTf29af420ec4b48d6a551b45d78d62e62/
- URN
urn:pkr-prod:CUTf29af420ec4b48d6a551b45d78d62e62
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.