Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal Stability
Two alternating copolymers of dithienosilole (DTS) were designed and synthesized with small optical band gaps, flanked by thienyl units as electron-donor moieties and benzothiadiazole dicarboxylic imide (BTDI) as electron-acceptor moieties. The BTDI moieties were anchored to two different solubilizi...
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2021-05-01
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| author | Ary R. Murad Elham M. A. Dannoun Shujahadeen B. Aziz Ahmed Iraqi Sozan N. Abdullah Muaffaq M. Nofal Ranjdar M. Abdullah |
| author_facet | Ary R. Murad Elham M. A. Dannoun Shujahadeen B. Aziz Ahmed Iraqi Sozan N. Abdullah Muaffaq M. Nofal Ranjdar M. Abdullah |
| author_sort | Ary R. Murad |
| collection | DOAJ |
| description | Two alternating copolymers of dithienosilole (DTS) were designed and synthesized with small optical band gaps, flanked by thienyl units as electron-donor moieties and benzothiadiazole dicarboxylic imide (BTDI) as electron-acceptor moieties. The BTDI moieties were anchored to two different solubilizing side chains, namely 3,7-dimethyloctyl and <i>n</i>-octyl chains. An analysis of the effect of the electrochemical, optical, thermal, and structural characteristics of the resulting polymers along with their solubility and molecular weight is the subject of this paper. The Stille polymerization was used to synthesize PDTSDTBTDI-DMO and PDTSDTBTDI-8. The average molecular weight of PDTSDTBTDI-DMO and PDTSDTBTDI-8 is 14,600 and 5700 g mol<sup>−1</sup>, respectively. Both polymers have shown equivalent optical band gaps around 1.4 eV. The highest occupied molecular orbital (HOMO) levels of the polymers were comparable, around −5.2 eV. The lowest unoccupied molecular orbital (LUMO) values were −3.56 and −3.45 eV for PDTSDTBTDI-DMO and PDTSDTBTDI-8, respectively. At decomposition temperatures above 350 °C, both copolymers showed strong thermal stability. The studies of powder X-ray diffraction (XRD) have shown that they are amorphous in a solid-state. |
| first_indexed | 2024-03-10T11:02:48Z |
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| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-03-10T11:02:48Z |
| publishDate | 2021-05-01 |
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| series | Applied Sciences |
| spelling | doaj.art-c3357c84b2904624b05e35d1665451e82023-11-21T21:22:42ZengMDPI AGApplied Sciences2076-34172021-05-011111486610.3390/app11114866Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal StabilityAry R. Murad0Elham M. A. Dannoun1Shujahadeen B. Aziz2Ahmed Iraqi3Sozan N. Abdullah4Muaffaq M. Nofal5Ranjdar M. Abdullah6Department of Pharmaceutical Chemistry, College of Medical and Applied Sciences, Charmo University, Chamchamal, Sulaimani 46023, IraqGeneral Science Department, Woman Campus, Prince Sultan University, P.O. Box 66833, Riyadh 11586, Saudi ArabiaHameed Majid Advanced Polymeric Materials Research Lab., Department of Physics, College of Science, University of Sulaimani, Qlyasan Street, Sulaimani 46001, IraqDepartment of Chemistry, University of Sheffield, Sheffield S3 7HF, UKDepartment of Chemistry, College of Science, University of Sulaimani, Qlyasan Street, Kurdistan Regional Government, Sulaimani 46001, IraqDepartment of Mathematics and General Sciences, Prince Sultan University, P.O. Box 66833, Riyadh 11586, Saudi ArabiaHameed Majid Advanced Polymeric Materials Research Lab., Department of Physics, College of Science, University of Sulaimani, Qlyasan Street, Sulaimani 46001, IraqTwo alternating copolymers of dithienosilole (DTS) were designed and synthesized with small optical band gaps, flanked by thienyl units as electron-donor moieties and benzothiadiazole dicarboxylic imide (BTDI) as electron-acceptor moieties. The BTDI moieties were anchored to two different solubilizing side chains, namely 3,7-dimethyloctyl and <i>n</i>-octyl chains. An analysis of the effect of the electrochemical, optical, thermal, and structural characteristics of the resulting polymers along with their solubility and molecular weight is the subject of this paper. The Stille polymerization was used to synthesize PDTSDTBTDI-DMO and PDTSDTBTDI-8. The average molecular weight of PDTSDTBTDI-DMO and PDTSDTBTDI-8 is 14,600 and 5700 g mol<sup>−1</sup>, respectively. Both polymers have shown equivalent optical band gaps around 1.4 eV. The highest occupied molecular orbital (HOMO) levels of the polymers were comparable, around −5.2 eV. The lowest unoccupied molecular orbital (LUMO) values were −3.56 and −3.45 eV for PDTSDTBTDI-DMO and PDTSDTBTDI-8, respectively. At decomposition temperatures above 350 °C, both copolymers showed strong thermal stability. The studies of powder X-ray diffraction (XRD) have shown that they are amorphous in a solid-state.https://www.mdpi.com/2076-3417/11/11/4866polymer synthesisdithienosilole-based copolymersstille polymerizationband gap studycyclic voltammetryUV-vis |
| spellingShingle | Ary R. Murad Elham M. A. Dannoun Shujahadeen B. Aziz Ahmed Iraqi Sozan N. Abdullah Muaffaq M. Nofal Ranjdar M. Abdullah Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal Stability Applied Sciences polymer synthesis dithienosilole-based copolymers stille polymerization band gap study cyclic voltammetry UV-vis |
| title | Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal Stability |
| title_full | Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal Stability |
| title_fullStr | Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal Stability |
| title_full_unstemmed | Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal Stability |
| title_short | Synthesis of Amorphous Conjugated Copolymers Based on Dithienosilole-Benzothiadiazole Dicarboxylic Imide with Tuned Optical Band Gaps and High Thermal Stability |
| title_sort | synthesis of amorphous conjugated copolymers based on dithienosilole benzothiadiazole dicarboxylic imide with tuned optical band gaps and high thermal stability |
| topic | polymer synthesis dithienosilole-based copolymers stille polymerization band gap study cyclic voltammetry UV-vis |
| url | https://www.mdpi.com/2076-3417/11/11/4866 |
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