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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Article number2300458
JournalMacromolecular Rapid Communications
Volume45
Issue number3
DOIs
Publication statusPublished - Feb 2024

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Funding

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).

FundersFunder number
Yükseköğretim Kurulu
Istanbul Teknik ÜniversitesiTGA‐2023‐44004

    Keywords

    • electrophilic aromatic substitution
    • manganese decacarbonyl
    • onium salt
    • photochemistry
    • visible light-induced polymerization

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