An Electron-Transporting Thiazole-Based Polymer Synthesized Through Direct (Hetero)Arylation Polymerization

Chávez, Patricia; Bulut, İbrahim; Fall, Sadiara; Ibraikulov, Olzhas A.; Chochos, Christos L.; Bartringer, J.; Heiser, T.; Lévêque, P.; Leclerc, Nicolas

doi:10.3390/molecules23061270

Cited by 7 publications

(5 citation statements)

References 32 publications

(37 reference statements)

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“…284 and 7 are both PUs with thiazole structures. This result is in agreement with previous work, which suggest that the low reorganization energy of thiazole can promote the hopping of electrons between units in OSC molecules, and the electron affinity of thiazole units is always higher than 3 eV and can reduce the barrier of electron injection. − PU No. 423 is a BTI structure and is an effective acceptor PU in n-type OSCs.…”

Section: Resultssupporting

confidence: 93%

Polymer-Unit Fingerprint (PUFp): An Accessible Expression of Polymer Organic Semiconductors for Machine Learning

Zhang

Wei

et al. 2023

ACS Appl. Mater. Interfaces

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High-performance organic semiconductors (OSCs) can be designed based on the identification of functional units and their role in the material properties. Herein, we present a polymer-unit fingerprint (PUFp) generation framework, “Python-based polymer-unit-recognition script” (PURS), to identify the subunits “polymer unit” in the polymer and generate polymer-unit fingerprint (PUFp). Using 678 collected OSC data, machine learning (ML) models can be used to determine structure–mobility relationships by using PUFp as a structural input, and the classification accuracy reaches 85.2%. A polymer-unit library consisting of 445 units is constructed, and the key polymer units affecting the mobility of OSCs are identified. By investigating the combinations of polymer units with mobility performance, a scheme for designing OSCs by combining ML approaches and PUFp information is proposed. This scheme not only passively predicts OSC mobility but also actively provides structural guidance for high-mobility OSC material design. The proposed scheme demonstrates the ability to screen materials through pre-evaluation and classification ML steps and is an alternative methodology for applying ML in high-mobility OSC discovery.

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Section: Resultssupporting

confidence: 93%

Polymer-Unit Fingerprint (PUFp): An Accessible Expression of Polymer Organic Semiconductors for Machine Learning

Zhang

Wei

et al. 2023

ACS Appl. Mater. Interfaces

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“…7 are both polymer units with thiazole structures. This result is in agreement with the results in previous work, in which the low reorganization energy of thiazole can promote the hopping of electrons between units in OSC molecules 53 , and the electron a nity of thiazole units is always higher than 3 eV and can reduce the barrier for electron injection [72][73][74][75] . Polymer unit No.…”

Section: Identi Cation Of Key Polymer Units That Greatly In Uence Osc...supporting

confidence: 93%

Data-based Polymer-Unit Fingerprint (PUFp): A Newly Accessible Expression of Polymer Organic Semiconductors for Machine Learning

Zhang

Wei

et al. 2022

Preprint

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In the process of finding high-performance organic semiconductors (OSCs), it is of paramount importance in material development to identify important functional units that play key roles in material performance and subsequently establish substructure-property relationships. Herein, we describe a polymer-unit fingerprint (PUFp) generation framework. Machine learning (ML) models can be used to determine structure-mobility relationships by using PUFp information as structural input with 678 pieces of collected OSC data, and the prediction accuracy reaches 83.9%. A polymer-unit library consisting of 445 units is constructed, and the key polymer units for the mobility of OSCs are identified. By investigating the combinations of polymer units with mobility performance, a scheme for designing polymer OSC materials by combining ML approaches and PUFp information is proposed to not only passively predict OSC mobility but also actively provide structural guidance for new high-mobility OSC material design. The proposed scheme demonstrates the ability to screen new materials through pre-evaluation and classification ML steps and is an alternative methodology for applying ML in new high-mobility OSC discovery.

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“…Since 10 mol % TMEDA resulted in the highest M n among the different TMEDA concentrations studied, increasing the monomer concentration with respect to IDT was an additional parameter varied to obtain higher M n . Previous studies have investigated the effects of M n as a function of monomer concentration and observed that high monomer concentrations led to higher M n . − These results corroborate with kinetic experiments performed by Fagnou and co-workers, concluding the first-order dependency of the C–H monomer concentration in the direct arylation mechanism . For our p(IDT–TIT) system, there was a slight increase in crude (i.e., before Soxhlet) M n from 13.9 to 15.2 kg/mol when the monomer concentration increased from 0.05 to 0.09 M, respectively; however, the M n isolated from the hexane fraction remained similar (Table , entries 3 and 6).…”

Section: Introductionsupporting

confidence: 90%

Direct Arylation Polymerization of Degradable Imine-Based Conjugated Polymers

Hsu,

Lin,

Uva

et al. 2023

Macromolecules

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The development and optimization of reliable polymerization methods are needed for the synthesis of degradable imine-based conjugated polymers, which are attractive materials for transient electronics. Direct arylation polymerization (DArP) has emerged as a sustainable and atom-economical synthetic method for the preparation of well-defined conjugated polymers. Compared to polymerization methods such as imine polycondensation or Stille cross-coupling polymerization, which require monomer functionalization, direct arylation proceeds via C–H activation and thereby reduces synthetic complexities and toxic byproducts. Here, we report the first use of DArP for the synthesis of an imine-based indacenodithiophene (IDT) copolymer, p(IDT–TIT). Polymers prepared via DArP can result in branched or cross-linked polymer chains due to the reactivity of C–H bonds in the monomers. In this report, we demonstrate a systematic study focusing on the reaction conditions needed to prepare p(IDT–TIT) via DArP with tetramethylethylenediamine as a coligand. The degradable polymer is characterized via nuclear magnetic resonance spectroscopy, high-temperature gel permeation chromatography, and ultraviolet–visible–near-infrared spectroscopy. With the simplicity of monomer preparation and reaction conditions, we anticipate that this efficient synthetic protocol will lead to higher synthetic adoption in the research community to aid the exploration of high-performance imine-based degradable materials.

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An Electron-Transporting Thiazole-Based Polymer Synthesized Through Direct (Hetero)Arylation Polymerization

Cited by 7 publications

References 32 publications

Polymer-Unit Fingerprint (PUFp): An Accessible Expression of Polymer Organic Semiconductors for Machine Learning

Polymer-Unit Fingerprint (PUFp): An Accessible Expression of Polymer Organic Semiconductors for Machine Learning

Data-based Polymer-Unit Fingerprint (PUFp): A Newly Accessible Expression of Polymer Organic Semiconductors for Machine Learning

Direct Arylation Polymerization of Degradable Imine-Based Conjugated Polymers

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