Backbone-driven host–dopant miscibility modulates molecular doping in NDI conjugated polymers

Villalva, Diego Rosas; Singh, Saumya; Galuska, Luke; Sharma, Anirudh; Han, Jianhua; Liu, Jian; Haque, Azimul; Jang, Soyeong; Emwas, Abdul Hamid; Koster, L. Jan Anton; Gu, Xiaodan; Schroeder, Bob C.; Baran, Derya

doi:10.1039/d1mh01357b

Cited by 9 publications

(19 citation statements)

References 45 publications

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“…2b illustrates the torsion energy for both trimers and it is found that the gNDI-V trimer gives a larger torsion energy barrier (∼0.69 eV) than the gNDI-T trimer (∼0.12 eV), enabling the gNDI-V trimer to have a more rigid backbone, since the hydrogen bond works as a non-bonding conformational lock. 43 Furthermore, the coplanar backbone would potentially prolong the coherent conjugation length and enhance interchain charge carrier transport. 57 Besides, the visualization of LUMOs and HOMOs is shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…41,42 Additionally, much potential was found in NDI-based copolymers as electrochromic displays and energy storage devices, which can be used as a platform for varied aqueous-based electrochemical devices. 16 However, the carbonyl groups in the NDI core often cause a strong steric hindrance with the adjacent units and a twisted backbone conformation, 43,44 consequently resulting in localized polaron and limited carrier transport. 45,46 For instance, our previous work investigated glycolated NDI coupling with bithiophene to give gNDI-BT, which was fabricated as a channel material in OECTs.…”

Section: Introductionmentioning

confidence: 99%

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Backbone coplanarity manipulation via hydrogen bonding to boost the n-type performance of polymeric mixed conductors operating in aqueous electrolyte

et al. 2023

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Backbone coplanarity manipulation via hydrogen bonding to boost the n-type performance of polymeric mixed conductors operating in aqueous electrolyte

et al. 2023

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“…Three NDI-containing copolymers of P1G, P2G, and P3G, based on bithiophene, vinylene, and acetylenic units, respectively, were compared in terms of energy levels, microstructure, and host:dopant miscibility. 65 Although polymer P3G showed the most planar structures among these π-CPs, its smallest dipole moment obstructs its miscibility and charge transfer with polar dopant molecules of N-DMBI. In contrast, P1G, possessing the most polar πbackbones, displayed the highest σ at a relatively low dopant concentration owing to its superior tolerance to dopants.…”

Section: Electrical Characteristicsmentioning

confidence: 97%

“…p-Type: D−π, − ,,,,,,,,− ,− A−π, − and D–A − ,,− structures. n-Type: A–A, ,,,,,,, A−π, − ,,,,− ,,− and D–A ,,,,,,,, structures.…”

Section: Correlating Polymeric Structures With Electrical Characteris...unclassified

“…A strong tolerance to dopant-induced disorders, or in other words, excellent host:dopant miscibility, is highly required. Three NDI-containing copolymers of P1G, P2G, and P3G, based on bithiophene, vinylene, and acetylenic units, respectively, were compared in terms of energy levels, microstructure, and host:dopant miscibility . Although polymer P3G showed the most planar structures among these π-CPs, its smallest dipole moment obstructs its miscibility and charge transfer with polar dopant molecules of N -DMBI.…”

Section: Correlating Polymeric Structures With Electrical Characteris...mentioning

confidence: 99%

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Strategic Insights into Semiconducting Polymer Thermoelectrics by Leveraging Molecular Structures and Chemical Doping

2022

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Thermoelectric (TE) materials can realize the direct transformation between heat and electricity, thereby facilitating the recycling of waste heat. Semiconducting π-conjugated polymers (π-CPs) have been largely explored as organic TE materials thanks to the facile molecular tunability of their electronic properties, their room-temperature solution-processability, their intrinsic low thermal conductivity, and their outstanding mechanical flexibility. In this Focus Review, we describe two key strategieschemical doping and structural tailoringin polymeric TEs for strengthening TE power factors of π-CPs. First, the doping mechanisms are unraveled by a sequential process of charge transfer and free carrier release, followed by the introduction of various doping methods for enhancing the chemical doping. Second, the design principles for polymeric structures including the π-backbone and side-chain engineering are presented. Third, supplementary strategies such as polymer chain alignment and construction of polymer blends are identified. Finally, the existing prime obstacles to future development are discussed and an outlook on feasible solutions to resolving them is provided.

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Intrinsically Stretchable Organic Thermoelectric Polymers Enabled by Incorporating Fused‐Ring Conjugated Breakers

Tseng,

Wang,

Lin

et al. 2024

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While research on organic thermoelectric polymers is making significant progress in recent years, realization of a single polymer material possessing both thermoelectric properties and stretchability for the next generation of self‐powered wearable electronics is a challenging task and remains an area yet to be explored. A new molecular engineering concept of “conjugated breaker” is employed to impart stretchability to a highly crystalline diketopyrrolepyrrole (DPP)‐based polymer. A hexacyclic diindenothieno[2,3‐b]thiophene (DITT) unit, with two 4‐octyloxyphenyl groups substituted at the tetrahedral sp3‐carbon bridges, is selected to function as the conjugated breaker that can sterically hinder intermolecular packing to reduce polymers’ crystallinity. A series of donor–acceptor random copolymers is thus developed via polymerizing the crystalline DPP units with the DITT conjugated breakers. By controlling the monomeric DPP/DITT ratios, DITT30 reaches the optimal balance of crystalline/amorphous regions, exhibiting an exceptional power factor (PF) value up to 12.5 µW m−1 K−2 after FeCl3‐doping; while, simultaneously displaying the capability to withstand strains exceeding 100%. More significantly, the doped DITT30 film possesses excellent mechanical endurance, retaining 80% of its initial PF value after 200 cycles of stretching/releasing at a strain of 50%. This research marks a pioneering achievement in creating intrinsically stretchable polymers with exceptional thermoelectric properties.

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Backbone-driven host–dopant miscibility modulates molecular doping in NDI conjugated polymers

Abstract: Molecular doping is the key to enabling organic electronic devices, however, the design strategies to maximize doping efficiency demands further clarity and comprehension.

Cited by 9 publications

References 45 publications

Backbone coplanarity manipulation via hydrogen bonding to boost the n-type performance of polymeric mixed conductors operating in aqueous electrolyte

Backbone coplanarity manipulation via hydrogen bonding to boost the n-type performance of polymeric mixed conductors operating in aqueous electrolyte

Strategic Insights into Semiconducting Polymer Thermoelectrics by Leveraging Molecular Structures and Chemical Doping

Intrinsically Stretchable Organic Thermoelectric Polymers Enabled by Incorporating Fused‐Ring Conjugated Breakers

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