Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer

Banu Köz

doi:10.18596/jotcsa.1981423

Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer

Abstract

3,4-Phenylenedioxythiophene (PheDOT) is an electron-rich heterocyclic building block that has attracted considerable interest for the preparation of conjugated organic materials. In this study, a series of dodecyl-substituted PheDOT derivatives was synthesized through lithiation–alkylation reactions. Both mono- and di-dodecyl-substituted PheDOT derivatives were obtained. The mono-substituted derivative was subsequently subjected to stannylation, affording a product assigned, on the basis of the reaction sequence and 1H NMR data, as the proposed tributylstannyl-PheDOT intermediate. The synthesized compounds were characterized using ¹H NMR, ¹³C NMR, and mass spectrometric techniques, depending on the data available for each compound. The alkylation reaction afforded 1,3-didodecylbenzo[b]thieno[3,4-e][1,4]dioxine (di-dodecyl-PheDOT) and 1-dodecylbenzo[b]thieno[3,4-e][1,4]dioxine (mono-dodecyl-PheDOT) in isolated yields of 8.2% and 32%, respectively. Under palladium-catalyzed coupling conditions, two PheDOT-based conjugated dimers, 3,3’-didodecyl-1,1’-bibenzo[b]thieno[3,4-e][1,4]dioxine (B2) and 3-dodecyl-1,1’-bibenzo[b]thieno[3,4-e][1,4]dioxine (B4) were isolated and characterized by spectroscopic analyses. The formation of these dimers supports the suitability of alkyl-functionalized PheDOT derivatives as precursors for the construction of larger π-conjugated structures. In addition, several PheDOT-derived conjugated structures and plausible coupling products were investigated using Density Functional Theory (DFT) calculations. The investigated systems were selected on the basis of experimentally observed mass spectrometric data and proposed coupling pathways. The incorporation of dodecyl substituents provided PheDOT derivatives that were sufficiently soluble in common organic solvents to allow chromatographic purification and spectroscopic characterization. These results expand the range of structurally defined alkyl-functionalized PheDOT derivatives and provide useful molecular building blocks for the future development of π-conjugated PheDOT-based systems.

Keywords

Supporting Institution

Council of Higher Education (YÖK), Türkiye, for financial support through a short-term overseas research scholarship at Bangor University, UK.

Project Number

30-M-16

Thanks

The author gratefully acknowledges the Council of Higher Education (YÖK), Türkiye, for financial support through a short-term overseas research scholarship at Bangor University, UK. The author sincerely thanks Prof. Igor F. Perepichka for his mentorship, scientific guidance, and valuable discussions during the research stay at Bangor University. The author also acknowledges the Scientific Research Projects Coordination Unit of Karamanoğlu Mehmetbey University (Project No. 30-M-16) for providing access to the Gaussian 09 software package.

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Details

Primary Language

English

Subjects

Organic Chemical Synthesis

Journal Section

Research Article

Authors

Banu Köz ^*
0000-0002-3774-7322
Türkiye

Publication Date

September 28, 2026

Submission Date

June 29, 2026

Acceptance Date

August 27, 2026

Published in Issue

Year 2026 Volume: 2026 Number: 2

DOI

https://doi.org/10.18596/jotcsa.1981423

IZ

https://izlik.org/JA87DR98GF

Cite

RIS / Bibtex

APA

Köz, B. (2026). Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer. Journal of the Turkish Chemical Society Section A: Chemistry, 2026(2), 1-15. https://doi.org/10.18596/jotcsa.1981423

AMA

1.Köz B. Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer. JOTCSA. 2026;2026(2):1-15. doi:10.18596/jotcsa.1981423

Chicago

Köz, Banu. 2026. “Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer”. Journal of the Turkish Chemical Society Section A: Chemistry 2026 (2): 1-15. https://doi.org/10.18596/jotcsa.1981423.

EndNote

Köz B (September 1, 2026) Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer. Journal of the Turkish Chemical Society Section A: Chemistry 2026 2 1–15.

IEEE

[1]B. Köz, “Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer”, JOTCSA, vol. 2026, no. 2, pp. 1–15, Sept. 2026, doi: 10.18596/jotcsa.1981423.

ISNAD

Köz, Banu. “Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer”. Journal of the Turkish Chemical Society Section A: Chemistry 2026/2 (September 1, 2026): 1-15. https://doi.org/10.18596/jotcsa.1981423.

JAMA

1.Köz B. Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer. JOTCSA. 2026;2026:1–15.

MLA

Köz, Banu. “Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer”. Journal of the Turkish Chemical Society Section A: Chemistry, vol. 2026, no. 2, Sept. 2026, pp. 1-15, doi:10.18596/jotcsa.1981423.

Vancouver

1.Banu Köz. Alkyl-Substituted PheDOT Derivatives and a PheDOT-Based Conjugated Dimer. JOTCSA. 2026 Sep. 1;2026(2):1-15. doi:10.18596/jotcsa.1981423

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