N-Unsubstituted thienoisoindigos: preparation, molecular packing and ambipolar organic field-effect transistors

Yoo, Dongho; Hasegawa, Tsukasa; Ashizawa, Minoru; Kawamoto, Tadashi; Masunaga, Hiroyasu; Hikima, Takaaki; Matsumoto, Hidetoshi; Mori, Takehiko

doi:10.1039/c7tc00327g

Cited by 26 publications

(36 citation statements)

References 44 publications

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“…This configuration is very similar to the geometries found in molecular crystals of thienoisoindigos with linear alkyl chains and is further supported by gas sorption analysis (see below). 30 , 31 …”

Section: Resultsmentioning

confidence: 99%

Fast-Switching Vis–IR Electrochromic Covalent Organic Frameworks

et al. 2021

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Electrochromic coatings are promising for applications in smart windows or energy-efficient optical displays. However, classical inorganic electrochromic materials such as WO 3 suffer from low coloration efficiency and slow switching speed. We have developed highly efficient and fast-switching electrochromic thin films based on fully organic, porous covalent organic frameworks (COFs). The low band gap COFs have strong vis–NIR absorption bands in the neutral state, which shift significantly upon electrochemical oxidation. Fully reversible absorption changes by close to 3 OD can be triggered at low operating voltages and low charge per unit area. Our champion material reaches an electrochromic coloration efficiency of 858 cm 2 C –1 at 880 nm and retains >95% of its electrochromic response over 100 oxidation/reduction cycles. Furthermore, the electrochromic switching is extremely fast with response times below 0.4 s for the oxidation and around 0.2 s for the reduction, outperforming previous COFs by at least an order of magnitude and rendering these materials some of the fastest-switching frameworks to date. This combination of high coloration efficiency and very fast switching reveals intriguing opportunities for applications of porous organic electrochromic materials.

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Section: Resultsmentioning

confidence: 99%

Fast-Switching Vis–IR Electrochromic Covalent Organic Frameworks

et al. 2021

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“…As further detailed in the Supporting Information, the polymers studied herein were synthesized using established synthetic methodologies by first constructing the isoindigo, 7,7'-diazaisoindigo and thienoisoindigo cores with amphipathic side chains comprising a fivemethylene spacer and a terminal triethylene glycol segment. [28,[32][33][34] Following bromination, the reactive monomers were subject to Stille polycondensation with 2,5-bis(trimethylstannyl)thiophene to afford thiophene copolymers IG-T, AIG-T and TIG-T and to Suzuki polycondensation with 2,1,3-benzothiadiazole-4,7-bis(boronic acid pinacol ester) to afford 2,1,3benzothiadiazole copolymers IG-BT, AIG-BT and TIG-BT. The crude polymers were purified by Soxhlet extractions, after which the polymers were obtained with estimated weight average molecular weights of 35 kDa, 29 kDa and 26 kDa for IG-BT, AIG-T and AIG-BT, respectively, as determined by gel permeation chromatography and further detailed in the SI.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

From p‐ to n‐Type Mixed Conduction in Isoindigo‐Based Polymers through Molecular Design

et al. 2022

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dominated by poly (3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT:PSS) and closely related derivatives as the active material, [4][5][6][7] new semiconducting materials have started to enter the arena in recent years. [8][9][10][11][12] In particular, hole-transporting (p-type) mixed conductors have emerged with properties on par or even better than benchmark PEDOT:PSS formulations, [9,13,14] whereas electron-transporting (n-type) materials are still lacking considerably in terms of mixed conduction performance. [15][16][17][18][19] The design of semiconducting materials for bioelectronic applications is heavily influenced by the rich body of literature in the broader field of organic electronics, evidenced by the development of, for example, oligo-and polythiophenes, [8,11,20,21] fullerenes, [18] diketopyrrolopyrrole-, [12,[22][23][24] and naphthalene-diimide-based [15,16] systems as efficient OMIECs. With that in mind, another versatile and highly efficient charge-transporting moiety, isoindigo (IG), has received very little attention for bioelectronic applications. [25] The IG motif depicted in Figure 1a can be structurally modified not only by introducing various solubilizing Organic mixed ionic and electronic conductors are of significant interest for bioelectronic applications. Here, three different isoindigoid building blocks are used to obtain polymeric mixed conductors with vastly different structural and electronic properties which can be further fine-tuned through the choice of comonomer unit. This work shows how careful design of the isoindigoid scaffold can afford highly planar polymer structures with high degrees of electronic delocalization, while subtle structural modifications can control the dominant charge carrier (hole or electron) when probed in organic electrochemical transistors. A combination of experimental and computational techniques is employed to probe electrochemical, structural, and mixed ionic and electronic properties of the polymer series which in turn allows the derivation of important structure-property relations for this promising class of materials in the context of organic bioelectronics. Ultimately, these findings are used to outline robust molecular-design strategies for isoindigo-based mixed conductors that can support efficient p-type, n-type, and ambipolar transistor operation in an aqueous environment.

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“…The transistors based on the dicyanated isoindigo displayed unipolar charge transport by modifying the dielectric with self‐assembled monolayers (SAMs) of n ‐tetradecylphosphonic acid (TPA) whereas it was interestingly noted that the device showed good ambipolar performance under the adoption of 12,12,13,13,14,14,15,15,16,16,17,17,18,18,18‐pentadecylfluorooctadecylphosphonic acid (FOPA) SAMs onto the insulating layer probably due to polarization effect of the electronegative fluorine atoms . Different substituents and substitutional positions together with modified insulating layers via various SAMs provide more possibilities to realize better performance ambipolar transistors on the basis of isoindigo derivatives …”

Section: Ambipolar Organic Semiconducting Materialsmentioning

confidence: 99%

Recent Advances in Ambipolar Transistors for Functional Applications

Ren

Yang

Zhou

et al. 2019

Adv Funct Materials

169

139

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Ambipolar transistors represent a class of transistors where positive (holes) and negative (electrons) charge carriers both can transport concurrently within the semiconducting channel. The basic switching states of ambipolar transistors are comprised of common off-state and separated on-state mainly impelled by holes or electrons. During the past years, diverse materials are synthesized and utilized for implementing ambipolar charge transport and their further emerging applications comprising ambipolar memory, synaptic, logic, and light-emitting transistors on account of their special bidirectional carrier-transporting characteristic. Within this review, recent developments of ambipolar transistor field involving fundamental principles, interface modifications, selected semiconducting material systems, device structures, ambipolar characteristics, and promising applications are highlighted. The existed challenges and prospective for researching ambipolar transistors in electronics and optoelectronics are also discussed. It is expected that the review and outlook are well timed and instrumental for the rapid progress of academic sector of ambipolar transistors in lighting, display, memory, as well as neuromorphic computing for artificial intelligence.

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N-Unsubstituted thienoisoindigos: preparation, molecular packing and ambipolar organic field-effect transistors

Abstract: N-Unsubstituted thienoisoindigo and the diphenyl derivative are prepared and these molecules exhibit ambipolar performance in organic thin film transistors.

Cited by 26 publications

References 44 publications

Fast-Switching Vis–IR Electrochromic Covalent Organic Frameworks

Fast-Switching Vis–IR Electrochromic Covalent Organic Frameworks

From p‐ to n‐Type Mixed Conduction in Isoindigo‐Based Polymers through Molecular Design

Recent Advances in Ambipolar Transistors for Functional Applications

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