Synthesis and Characterization of n-Doped Poly(benzodifurandione) (n-PBDF) Derivatives via Aromatic Substitution

IF 5.1 1区化学 Q1 POLYMER SCIENCE

Macromolecules Pub Date : 2024-11-13 DOI:10.1021/acs.macromol.4c02386

Mustafa H. Ahmed, Jinhyo Hwang, Bufan Xiao, Matthew R. Schiavone, Jagrity Chaudhary, Min Chen, Jianguo Mei

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Abstract

n-Doped poly(benzodifurandione) (n-PBDF) is an n-type conducting polymer with characteristics such as high electrical conductivity, solution processability, and weathering stability. Here, we systematically investigate the structure property relationship on the impact of structural modifications through aromatic substitution on the photophysical, electrical, and structural properties of n-PBDF and its oligomeric derivatives. We demonstrated that an electron donation group (methyl) raised the highest occupied molecular orbital energy level (+0.15 eV), while electron-withdrawing halogens (Br and Cl) decreased the lowest unoccupied molecular orbital energy level (−0.12 and −0.13 eV, respectively) in the polymers. Additionally, in both the undoped and doped oligomeric systems, these substitutions introduce large torsion angles (θ > 17°), causing the material to twist significantly. Moreover, the methyl-substituted polymer, n-PBDF-Me, was evaluated for its potential as a transparent organic conductor, due to its high optical transmittance (T₅₅₀ > 93%). However, n-PBDF-Me films have significantly lower conductivity than n-PBDF (0.40 vs 1330 S/cm) at similar thickness.

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通过芳香族取代合成 n 掺杂聚（苯并二呋喃二酮）（n-PBDF）衍生物并确定其特性

n 掺杂聚（苯并二呋喃二酮）（n-PBDF）是一种 n 型导电聚合物，具有高导电性、溶液加工性和耐候稳定性等特点。在此，我们系统地研究了通过芳香族取代进行结构修饰对 n-PBDF 及其低聚衍生物的光物理、电学和结构特性的影响。我们发现，电子捐献基团（甲基）提高了聚合物的最高占有分子轨道能级（+0.15 eV），而电子抽离卤素（溴和氯）则降低了聚合物的最低未占有分子轨道能级（分别为-0.12 和-0.13 eV）。此外，在未掺杂和掺杂的低聚物体系中，这些取代物引入了较大的扭转角（θ >17°），导致材料明显扭曲。此外，由于甲基取代聚合物 n-PBDF-Me 具有很高的透光率（T550 >93%），因此对其作为透明有机导体的潜力进行了评估。然而，在厚度相似的情况下，n-PBDF-Me 薄膜的导电率明显低于 n-PBDF（0.40 vs 1330 S/cm）。

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来源期刊

Macromolecules 工程技术-高分子科学

CiteScore

9.30

自引率

16.40%

发文量

942

审稿时长

2 months

期刊介绍： Macromolecules publishes original, fundamental, and impactful research on all aspects of polymer science. Topics of interest include synthesis (e.g., controlled polymerizations, polymerization catalysis, post polymerization modification, new monomer structures and polymer architectures, and polymerization mechanisms/kinetics analysis); phase behavior, thermodynamics, dynamic, and ordering/disordering phenomena (e.g., self-assembly, gelation, crystallization, solution/melt/solid-state characteristics); structure and properties (e.g., mechanical and rheological properties, surface/interfacial characteristics, electronic and transport properties); new state of the art characterization (e.g., spectroscopy, scattering, microscopy, rheology), simulation (e.g., Monte Carlo, molecular dynamics, multi-scale/coarse-grained modeling), and theoretical methods. Renewable/sustainable polymers, polymer networks, responsive polymers, electro-, magneto- and opto-active macromolecules, inorganic polymers, charge-transporting polymers (ion-containing, semiconducting, and conducting), nanostructured polymers, and polymer composites are also of interest. Typical papers published in Macromolecules showcase important and innovative concepts, experimental methods/observations, and theoretical/computational approaches that demonstrate a fundamental advance in the understanding of polymers.