Thienothiophene-Based Organic Porous Polymers Combining Different Linkers and Functional Groups: Design, Synthesis, Photophysical, and Charge Transport Properties

Melis Unal; Recep Isci; Ilknur Demirtas; Erdal Ertas; Rajendra Prasad Paitandi; Wakana Matsuda; Shu Seki; Turan Ozturk

doi:10.1002/ajoc.202500339

Thienothiophene-Based Organic Porous Polymers Combining Different Linkers and Functional Groups: Design, Synthesis, Photophysical, and Charge Transport Properties

Melis Unal
, Recep Isci
, Ilknur Demirtas
, Erdal Ertas^*
, Rajendra Prasad Paitandi
, Wakana Matsuda
, Shu Seki^*
, Turan Ozturk^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University
Scientific and Technological Research Council of Turkey
Kyoto University

Research output: Contribution to journal › Article › peer-review

Abstract

Organic covalent frameworks (COFs) are essential for various applications, including solar cells, capacitors, hydrogen production, cancer therapy, bacterial treatment, chemical sensors, and light-emitting diodes. This study presents the design and synthesis of novel conjugated triazine-type porous polymers (P1–P6) and their conjugated monomers (M1--M6), incorporating thienothiophene (TT) rings as π-bridges, along with cyanophenyl, phenyl, and heptyl as different functional groups, and triphenylamine (TPA), tetraphenylethylene (TPE), and carbazole (Cbz) as linkers. The polymers were synthesized via acid-catalyzed trimerization. Photo-injected charge carriers of the polymers and impact of molecular doping on the conductivities with iodine doping were analyzed. The highest photoconductivity, φ∑μ, reached 2.4 × 10⁻⁸ m² V⁻¹ s⁻¹ when doped with I₂ for the heptyl chain-substituted P6 (Cbz-linkage) among the analyzed porous polymers.

Original language	English
Article number	e00339
Journal	Asian Journal of Organic Chemistry
Volume	14
Issue number	9
DOIs	https://doi.org/10.1002/ajoc.202500339
Publication status	Published - Sept 2025

Bibliographical note

Publisher Copyright:
© 2025 The Author(s). Asian Journal of Organic Chemistry published by Wiley-VCH GmbH.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being
SDG 7 Affordable and Clean Energy

Keywords

Charge transport
Organic electronics
Porous materials
Thienothiophene
Triazine frameworks

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10.1002/ajoc.202500339

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title = "Thienothiophene-Based Organic Porous Polymers Combining Different Linkers and Functional Groups: Design, Synthesis, Photophysical, and Charge Transport Properties",

abstract = "Organic covalent frameworks (COFs) are essential for various applications, including solar cells, capacitors, hydrogen production, cancer therapy, bacterial treatment, chemical sensors, and light-emitting diodes. This study presents the design and synthesis of novel conjugated triazine-type porous polymers (P1–P6) and their conjugated monomers (M1--M6), incorporating thienothiophene (TT) rings as π-bridges, along with cyanophenyl, phenyl, and heptyl as different functional groups, and triphenylamine (TPA), tetraphenylethylene (TPE), and carbazole (Cbz) as linkers. The polymers were synthesized via acid-catalyzed trimerization. Photo-injected charge carriers of the polymers and impact of molecular doping on the conductivities with iodine doping were analyzed. The highest photoconductivity, φ∑μ, reached 2.4 × 10−8 m2 V−1 s−1 when doped with I2 for the heptyl chain-substituted P6 (Cbz-linkage) among the analyzed porous polymers.",

keywords = "Charge transport, Organic electronics, Porous materials, Thienothiophene, Triazine frameworks",

author = "Melis Unal and Recep Isci and Ilknur Demirtas and Erdal Ertas and Paitandi, \{Rajendra Prasad\} and Wakana Matsuda and Shu Seki and Turan Ozturk",

note = "Publisher Copyright: {\textcopyright} 2025 The Author(s). Asian Journal of Organic Chemistry published by Wiley-VCH GmbH.",

year = "2025",

month = sep,

doi = "10.1002/ajoc.202500339",

language = "English",

volume = "14",

journal = "Asian Journal of Organic Chemistry",

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T2 - Design, Synthesis, Photophysical, and Charge Transport Properties

AU - Unal, Melis

AU - Isci, Recep

AU - Demirtas, Ilknur

AU - Ertas, Erdal

AU - Paitandi, Rajendra Prasad

AU - Matsuda, Wakana

AU - Seki, Shu

AU - Ozturk, Turan

PY - 2025/9

Y1 - 2025/9

N2 - Organic covalent frameworks (COFs) are essential for various applications, including solar cells, capacitors, hydrogen production, cancer therapy, bacterial treatment, chemical sensors, and light-emitting diodes. This study presents the design and synthesis of novel conjugated triazine-type porous polymers (P1–P6) and their conjugated monomers (M1--M6), incorporating thienothiophene (TT) rings as π-bridges, along with cyanophenyl, phenyl, and heptyl as different functional groups, and triphenylamine (TPA), tetraphenylethylene (TPE), and carbazole (Cbz) as linkers. The polymers were synthesized via acid-catalyzed trimerization. Photo-injected charge carriers of the polymers and impact of molecular doping on the conductivities with iodine doping were analyzed. The highest photoconductivity, φ∑μ, reached 2.4 × 10−8 m2 V−1 s−1 when doped with I2 for the heptyl chain-substituted P6 (Cbz-linkage) among the analyzed porous polymers.

AB - Organic covalent frameworks (COFs) are essential for various applications, including solar cells, capacitors, hydrogen production, cancer therapy, bacterial treatment, chemical sensors, and light-emitting diodes. This study presents the design and synthesis of novel conjugated triazine-type porous polymers (P1–P6) and their conjugated monomers (M1--M6), incorporating thienothiophene (TT) rings as π-bridges, along with cyanophenyl, phenyl, and heptyl as different functional groups, and triphenylamine (TPA), tetraphenylethylene (TPE), and carbazole (Cbz) as linkers. The polymers were synthesized via acid-catalyzed trimerization. Photo-injected charge carriers of the polymers and impact of molecular doping on the conductivities with iodine doping were analyzed. The highest photoconductivity, φ∑μ, reached 2.4 × 10−8 m2 V−1 s−1 when doped with I2 for the heptyl chain-substituted P6 (Cbz-linkage) among the analyzed porous polymers.

KW - Charge transport

KW - Organic electronics

KW - Porous materials

KW - Thienothiophene

KW - Triazine frameworks

UR - https://www.scopus.com/pages/publications/105010699990

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DO - 10.1002/ajoc.202500339

M3 - Article

AN - SCOPUS:105010699990

SN - 2193-5807

VL - 14

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 9

M1 - e00339

ER -

Thienothiophene-Based Organic Porous Polymers Combining Different Linkers and Functional Groups: Design, Synthesis, Photophysical, and Charge Transport Properties

Abstract

Bibliographical note

UN SDGs

Keywords

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