A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties

Recep Isci

doi:10.17776/csj.1890613

A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties

Abstract

A novel conjugated porous polymer (CPP) based on thieno[3,2-b]thiophene (TT) and tetraphenylethylene (TPE) was successfully designed and synthesized via a Pd(0)-catalyzed Suzuki cross-coupling reaction. Owing to its rigid, highly cross-linked architecture, the resulting TT–TPE polymer is insoluble and exhibits permanent porosity. Comprehensive characterization using UV–Vis, fluorescence, and FTIR spectroscopy, together with scanning electron microscopy (SEM), cyclic voltammetry (CV), and thermogravimetric analysis (TGA), confirmed the successful formation of a robust π-conjugated porous network. The polymer exhibits a strong π–π* absorption band at 392 nm, intense fluorescence emission at 549 nm, and a large Stokes shift, indicating efficient intramolecular energy transfer and significant excited-state relaxation. SEM images reveal a hierarchically porous, sponge-like morphology, while electrochemical studies demonstrate stable redox behavior and favorable HOMO and LUMO energy levels, highlighting its potential for optoelectronic applications. Furthermore, the optical and electrochemical band gaps are in good agreement, indicating the reliability of the experimental results. Density functional theory (DFT) calculations further corroborate the experimental findings, showing excellent agreement between the simulated and observed electronic transitions. Overall, the TT–TPE conjugated porous polymer represents a promising functional material for applications in chemical sensing, energy storage, and optoelectronic devices.

Keywords

Functional polymer, Organic electronics, Porous polymer, Tetraphenylethylene, Thienothiophene

Thanks

I thank Istanbul Technical University (ITU) for financial support.

References

Long X., Li D., Wang B., Jiang Z., Xu W., Wang B., Yang D., Xia Y., Heterocyclization Strategy for Construction of Linear Conjugated Polymers: Efficient Metal-Free Electrocatalysts for Oxygen Reduction, Angew. Chem. Int. Ed., 58(33) (2019) 11369–11373. https://doi.org/10.1002/anie.201905468
Isci R., Balkan T., Tafazoli S., Sütay B., Eroglu M.S., Ozturk T., Thienothiophene and Triphenylbenzene Based Electroactive Conjugated Porous Polymer for Oxygen Reduction Reaction (ORR), ACS Appl. Energy Mater., 5(11) (2022) 13284–13292. https://doi.org/10.1021/acsaem.2c01830
Ma L., Liu Y., Liu Y., Jiang S., Li P., Hao Y., Shao P., Yin A., Feng X., Wang B., Ferrocene-Linkage-Facilitated Charge Separation in Conjugated Microporous Polymers, Angew. Chem. Int. Ed., 58(13) (2019) 4221–4226. https://doi.org/10.1002/anie.201813598
Isci R., Gencosman E., Yagci Y., Ozturk T., Thienothiophene and Biphenyl Based Conjugated Porous Polymer as a Photocatalyst for Visible Light Induced Free Radical and Cationic Polymerization, J. Photochem. Photobiol. A: Chem., 449 (2024) 115427. https://doi.org/10.1016/j.jphotochem.2023.115427
Isci R., Bildirir H., Gunturkun D., Gomez-Mendoza M., Liras M., A Thienothiophene and Anthracene Based Functional Hyperbranched Polymer: Synthesis, Photophysical Properties and Photocatalytic Studies, J. Mater. Chem. C, 12(39) (2024) 16108–16111. https://doi.org/10.1039/D4TC02568G
He S., Wen J., Cao B., Shi G., Zhang M., Porous Material-Based Electronic Noses for the Sensing of Volatile Organic Compounds, ACS Appl. Mater. Interfaces, 17(44) (2025) 60055–60103. https://doi.org/10.1021/acsami.5c17506
M’Baye G., Klymchenko A.S., Yushchenko D.A., Shvadchak V.V., Ozturk T., Fluorescent Dyes Undergoing Intramolecular Proton Transfer with Improved Sensitivity to Surface Charge in Lipid Bilayers, Photochem. Photobiol. Sci., 6(1) (2007) 71–76. https://doi.org/10.1039/b611699j
Fang M., Zhou J., Fei H., Yang K., He R., Porous-Material-Based Composite Phase Change Materials for a Lithium-Ion Battery Thermal Management System, Energy Fuels, 36(8) (2022) 4153–4173. https://doi.org/10.1021/acs.energyfuels.1c04444
Shi Y., Yang J., Gao F., Zhang Q., Covalent Organic Frameworks: Recent Progress in Biomedical Applications, ACS Nano, 17(3) (2023) 1879–1905. https://doi.org/10.1021/acsnano.2c11346
Ingle D.S., Babu D.J., Rao K.V., Synthesis of Near-Infrared-Absorbing Superhydrophilic Conjugated Porous Polymer via Postsynthetic Modification for Efficient Solar Steam Generation, ACS Appl. Energy Mater., 8(12) (2025) 8500–8507. https://doi.org/10.1021/acsaem.5c01044

Qi L., Qiao J., Design of Switchable Enzyme Carriers Based on Stimuli-Responsive Porous Polymer Membranes for Bioapplications, ACS Appl. Bio Mater., 4(6) (2021) 4706–4719. https://doi.org/10.1021/acsabm.1c00338
Wu D., Xu F., Sun B., Fu R., He H., Design and Preparation of Porous Polymers, Chem. Rev., 112(7) (2012) 3959–4015. https://doi.org/10.1021/cr200440z
Zhang H., Li H., Xu C.C., Yang S., Heterogeneously Chemo/Enzyme-Functionalized Porous Polymeric Catalysts of High Performance for Efficient Biodiesel Production, ACS Catal., 9(12) (2019) 10990–11029. https://doi.org/10.1021/acscatal.9b02748
Tian Y., Zhu G., Porous Aromatic Frameworks (PAFs), Chem. Rev., 120(16) (2020) 8934–8986. https://doi.org/10.1021/acs.chemrev.9b00687
Bronstein H., Chen Z., Ashraf R.S., Zhang W., Du J., Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices, J. Am. Chem. Soc., 133 (2011) 3272–3275. https://doi.org/10.1021/ja110619k
Tang W., Ke L., Tan L., Lin T., Kietzke T., Conjugated Copolymers Based on Fluorene-Thieno[3,2-b]thiophene for Light-Emitting Diodes and Photovoltaic Cells, Macromolecules, 40(17) (2007) 6164–6171. https://doi.org/10.1021/ma070575h
Eroglu M.S., Hazer B., Ozturk T., Caykara T., Hydroxylation of Pendant Vinyl Groups of Poly(3-Hydroxy Undec-10-Enoate) in High Yield, J. Appl. Polym. Sci., 97(5) (2005) 2132–2139. https://doi.org/10.1002/app.21943
Ozturk S.E., Isci R., Faraji S., Sütay B., Majewski L.A., Synthesis, Photophysical Properties and OFET Application of Thienothiophene and Benzothiadiazole Based Donor-π-Acceptor-π Type Conjugated Polymers, Eur. Polym. J., 191 (2023) 112028. https://doi.org/10.1016/j.eurpolymj.2023.112028
Isci R., Yavuz O., Faraji S., Gunturkun D., Eroglu M., Highly Sensitive OFET-Based Room-Temperature Operated Gas Sensors Using a Thieno[3,2-b]thiophene Extended Phthalocyanine Semiconductor, J. Mater. Chem. C, 13 (2025) 472–483. https://doi.org/10.1039/D4TC03208J
Suerkan A., Isci R., Ozturk T., Yagci Y., Cationic and Radical Polymerization Using a Boron–Thienothiophene–Triphenylamine Based D–π–A Type Photosensitizer under White LED Irradiation, Mol. Syst. Des. Eng., 8(10) (2023) 1319–1326. https://doi.org/10.1039/D3ME00083D
Fuchibe K., Mukohara I., Yamada A., Miyazaki D., Takayama R., Ichikawa J., Construction of Thienothiophene and Thienofuran Ring Systems via Ring Expansion of Difluorothiiranes Generated from Dithioesters, Org. Lett., 24(1) (2022) 169–174. https://doi.org/10.1021/acs.orglett.1c03805
Beyazit S., Aydogan B., Osken I., Ozturk T., Yagci Y., Long Wavelength Photoinitiated Free Radical Polymerization Using Conjugated Thiophene Derivatives in the Presence of Onium Salts, Polym. Chem., 2(5) (2011) 1185–1190. https://doi.org/10.1039/C1PY00019E.
Isci R., Unal M., Kucukcakir G., Gurbuz N.A., Gorkem S.F., Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties, J. Phys. Chem. B, 125(48) (2021) 13309–13319. https://doi.org/10.1021/acs.jpcb.1c09448
Isci R., Ozturk T., Thienothiophene-Based Organic Light-Emitting Diode: Synthesis, Photophysical Properties and Application, Beilstein J. Org. Chem., 19(1) (2023) 1849–1857. https://doi.org/10.3762/bjoc.19.137
Zhao S.S., Wang S.H., Sun Q., Zhang H., Zhao J.W., Fluorescent Tetraphenylethylene-Based Cerium Metal–Organic Frameworks for White-Light-Emitting Diodes, ACS Appl. Mater. Interfaces, 16(43) (2024) 58891–58897. https://doi.org/10.1021/acsami.4c14046
Hu H., Zeng D., Ming J.B., Yan Y., Wang W., Highly Efficient Multicolor-Emitting Tetraphenylethylene-Based Organic Salts with Commercialization Prospects, ACS Appl. Mater. Interfaces, 16(28) (2024) 36851–36861. https://doi.org/10.1021/acsami.4c03180
La D.D., Bhosale S.V., Jones L.A., Bhosale S.V., Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications, ACS Appl. Mater. Interfaces, 10(15) (2018) 12189–12216. https://doi.org/10.1021/acsami.7b12320
Saraswathi S.K., Joseph J., Thymine-Induced Dynamic Switching of Self-Assembled Nanofibers in Diaminotriazine-Functionalized Tetraphenylethylene Derivatives, ACS Appl. Nano Mater., 5(2) (2022) 3018–3027. https://doi.org/10.1021/acsanm.2c00310
Unal M., Isci R., Demirtas I., Ertas E., Matsuda W., Impact of Doping on Charge Transport Properties in Thienothiophene-Based Organic Porous Polymers, Macromol. Mater. Eng., 310(8) (2025) 2500033. https://doi.org/10.1002/mame.202500033
Bian L., Liang Y., Liu Z., Tetraphenylethylene-Incorporated Macrocycles and Nanocages: Construction and Applications, ACS Appl. Nano Mater., 5(10) (2022) 13940–13958. https://doi.org/10.1021/acsanm.2c01250
Unal M., Isci R., Demirtas I., Ertas E., Paitandi R.P., Thienothiophene-Based Organic Porous Polymers Combining Different Linkers and Functional Groups: Design, Synthesis, Photophysical, and Charge Transport Properties, Asian J. Org. Chem., 14(9) (2025) e00339. https://doi.org/10.1002/ajoc.202500339
Unal M., Isci R., Demirtas I., Ertas E., Paitandi R.P., Thienothiophene and Triazine Decorated Conjugated Materials Incorporating Various Functional Groups: Design, Synthesis, Photophysical and Charge Transport Properties, J. Mol. Struct., 1348(2) (2025) 143540. https://doi.org/10.1016/j.molstruc.2025.143540
Yildirim O., Tsaturyan A., Damin A., Nejrotti S., Crocellà V., Quinoid-Thiophene-Based Covalent Organic Polymers for High Iodine Uptake, ACS Appl. Mater. Interfaces, 15(12) (2023) 15819–15831. https://doi.org/10.1021/acsami.2c20853
Suna G., Gunduz S., Topal S., Ozturk T., Karakus E., A Unique Triple-Channel Fluorescent Probe for Discriminative Detection of Cyanide, Hydrazine, and Hypochlorite, Talanta, 257 (2023) 124365. https://doi.org/10.1016/j.talanta.2023.124365
Dalapati S., Jin E., Addicoat M., Heine T., Jiang D., Highly Emissive Covalent Organic Frameworks, J. Am. Chem. Soc., 138(18) (2016) 5797–5800. https://doi.org/10.1021/jacs.6b02700
Yu M., Xu N., Cai X.M., Liu H., Han S., Macroscopic and Fluorescence Detection of Reactive Oxygen Species by Using a Glucose-Linked Tetraphenylethylene Polymer Gel, New J. Chem., 47 (2023) 8484–8488. https://doi.org/10.1039/D3NJ00885A
Taylor D., Dalgarno S.J., Xu Z., Vilela F., Conjugated Porous Polymers: Incredibly Versatile Materials with Far-Reaching Applications, Chem. Soc. Rev., 49 (2020) 3981–4042. https://doi.org/10.1039/C9CS00315K
Che S., Fang L., Porous Ladder Polymer Networks, Chem, 6(10) (2020) 2558–2590. https://doi.org/10.1016/j.chempr.2020.08.002
Isci R., Tekin E., Kaya K., Mucur P.S., Gorkem S.F., Tetraphenylethylene Substituted Thienothiophene and Dithienothiophene Derivatives: Synthesis, Optical Properties and OLED Applications, J. Mater. Chem. C, 8 (2020) 7908–7915. https://doi.org/10.1039/D0TC01715A
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., et al. (2016). Gaussian 16. Gaussian, Inc. https://gaussian.com/gaussian16/

Details

Primary Language

English

Subjects

Physical Organic Chemistry, Organic Chemistry (Other)

Journal Section

Research Article

Authors

Recep Isci ^*
0000-0003-3086-4478
Türkiye

Publication Date

October 27, 2026

Submission Date

February 17, 2026

Acceptance Date

September 4, 2026

Published in Issue

Year 2026 Volume: 47 Number: 5

DOI

https://doi.org/10.17776/csj.1890613

IZ

https://izlik.org/JA78XF49KW

APA

Isci, R. (2026). A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties. Cumhuriyet Science Journal, 47(5), 821-828. https://doi.org/10.17776/csj.1890613

AMA

1.Isci R. A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties. CSJ. 2026;47(5):821-828. doi:10.17776/csj.1890613

Chicago

Isci, Recep. 2026. “A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties”. Cumhuriyet Science Journal 47 (5): 821-28. https://doi.org/10.17776/csj.1890613.

EndNote

Isci R (October 1, 2026) A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties. Cumhuriyet Science Journal 47 5 821–828.

IEEE

[1]R. Isci, “A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties”, CSJ, vol. 47, no. 5, pp. 821–828, Oct. 2026, doi: 10.17776/csj.1890613.

ISNAD

Isci, Recep. “A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties”. Cumhuriyet Science Journal 47/5 (October 1, 2026): 821-828. https://doi.org/10.17776/csj.1890613.

JAMA

1.Isci R. A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties. CSJ. 2026;47:821–828.

MLA

Isci, Recep. “A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties”. Cumhuriyet Science Journal, vol. 47, no. 5, Oct. 2026, pp. 821-8, doi:10.17776/csj.1890613.

Vancouver

1.Recep Isci. A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties. CSJ. 2026 Oct. 1;47(5):821-8. doi:10.17776/csj.1890613

As of 2026, Cumhuriyet Science Journal will be published in six issues per year, released in February, April, June, August, October, and December

A Porous Polymer of Thienothiophene and Tetraphenylethylene: Design, Synthesis and Photophysical Properties

Abstract

Keywords

Thanks

References

Details

Primary Language

Subjects

Journal Section

Authors

Publication Date

Submission Date

Acceptance Date

Published in Issue

DOI

IZ

Cite