Visible Light-Induced Synthesis of Conjugated Poly(phenylene butadiynylene) by a Combination of Halide Abstraction and Coupling Reactions

Busra Nakipoglu, Cansu Aydogan, Mücahit Özdemir, Yusuf Yagci*, Sermet Koyuncu*, Baris Kiskan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

This study describes a simple and efficient method for synthesizing conjugated poly(phenylene butadiynylene) (PPB)polymers using photo-induced radical homocoupling. The approach involves irradiating 1,4-bis(bromoethynyl)benzene with visible light in the presence of dimanganese decacarbonyl (Mn2(CO)10), which acts as a radical generator by abstracting halides and promoting subsequent radical coupling reactions. The resulting conjugated PPB exhibited a remarkable red shift, and the optical band gap decreased from −2.76 to −2.27 eV. A similar effect was observed in the electrochemically measured oxidation potential; the highest occupied molecular orbital position regressed from −6.06 to −5.69 eV. Transmission electron microscopy and atomic force microscopy measurements revealed the self-organization of the polymers to planar 2D nanorods, and the 2D structures of the polymers were further supported by density functional theory calculations. Moreover, the surface area of the polymer was found to be 53.61 and 30.69 m2/g according to Brunauer-Emmett-Teller and Barrett-Joyner-Halenda methods, respectively.

Original languageEnglish
Pages (from-to)6267-6275
Number of pages9
JournalMacromolecules
Volume56
Issue number16
DOIs
Publication statusPublished - 22 Aug 2023

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

Funding

Istanbul Technical University Research Fund (Project no. TGA-2023-44004). The authors would like to acknowledge the financial support from Istanbul Technical University Research Fund (Project no. TGA-2023-44004). One of the authors (Busra Nakipoglu) would like to thank the Council of Higher Education of Turkey for the 100/2000 CoHE Doctoral Scholarship and the TUBITAK 2211-A National Graduate Scholarship for financial support.

FundersFunder number
Council of Higher Education of Turkey
Istanbul Technical University Research Fund
Türkiye Bilimsel ve Teknolojik Araştırma Kurumu
Istanbul Teknik ÜniversitesiTGA-2023-44004

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