Exploiting Visible-Light Induced Radical to Cation Transformation Pathway for Reactivity Enhanced Electrophilic Aromatic Substitution Polymerization of Heteroaromatics

Emirhan Gencosman, Huseyin Cem Kiliclar*, Pawel Fiedor, Gorkem Yilmaz*, Joanna Ortyl, Yusuf Yagci, Baris Kiskan*

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Özet

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.

Orijinal dilİngilizce
Makale numarası2300458
DergiMacromolecular Rapid Communications
Hacim45
Basın numarası3
DOI'lar
Yayın durumuYayınlandı - Şub 2024

Bibliyografik not

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Finansman

The authors would like to acknowledge the financial support from the Council of Higher Education (YÖK) – Istanbul Technical University Research Fund YAP (Project Number: TGA‐2023‐44004).

FinansörlerFinansör numarası
Yükseköğretim Kurulu
Istanbul Teknik ÜniversitesiTGA‐2023‐44004

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