Simple Synthesis of Conjugated Polymers Enabled via Pyrrolo[3,2-b]pyrroles DOI
Kenneth‐John J. Bell,

Allison M. Kisiel,

Evan M. Smith

и другие.

Chemistry of Materials, Год журнала: 2022, Номер 34(19), С. 8729 - 8739

Опубликована: Сен. 27, 2022

Accessing conjugated polymers suitable for applications ranging from organic photovoltaics to bioelectronics through simple synthetic protocols is desirable the polymer community, as many systems that meet device performance metrics require arduous protocols. To simplify and minimize monomer steps, a dibrominated dihydropyrrolopyrrole was synthesized in air using single step did not column chromatography purification. Subsequently, first example of an electron-rich pyrrolopyrrole being polymerized accomplished via direct arylation polymerization dioxythiophene comonomer access alternating copolymer total three steps. The resulting exhibits absorbance high-energy portion visible spectrum solution solid state, relatively low onset oxidation (∼0.6 V vs Ag/AgCl), yellow-to-black electrochromism. Finally, complexity calculated, pyrrolopyrrole-co-dioxythiophene less synthetically complex when compared find applicability These findings demonstrate viability incorporating dihydropyrrolopyrroles into repeat unit structure metal-catalyzed cross-coupling reactions highlight their potential offer alternative current state-of-the-art polymers.

Язык: Английский

Organic mixed conductors for electrochemical transistors DOI Creative Commons
Joshua Tropp, Dilara Meli, Jonathan Rivnay

и другие.

Matter, Год журнала: 2023, Номер 6(10), С. 3132 - 3164

Опубликована: Май 24, 2023

Язык: Английский

Процитировано

52

Recent developments in indacenodithiophene and indacenodithienothiophene-based donor-acceptor conjugated polymers: From design to device performance in organic electronics DOI Creative Commons
Wissem Khelifi, Christine K. Luscombe

Progress in Polymer Science, Год журнала: 2024, Номер 151, С. 101804 - 101804

Опубликована: Фев. 23, 2024

Polymeric semiconductors based on donor-acceptor (D-A) conjugated polymers have emerged as a promising class of materials for various applications due to their excellent solution processability, low cost, and intrinsic flexibility. The use the indacenodithiophene (IDT) unit building block has received significant attention its unique pentacyclic ring structure exceptional photophysical electronic properties. This review focuses latest progress in field IDT-based polymers. We discuss versatility IDT structural molecular engineering tool, along with electron-deficient acceptors comonomers modifications unit. These advancements led improved device performance, particularly organic electronics such photodetectors, solar cells, field-effect transistors, thermoelectric devices. In summary, this serves valuable reference researchers who are interested creating high-performance polymeric using range optoelectronic

Язык: Английский

Процитировано

21

Mixed Ionic–Electronic Conduction, a Multifunctional Property in Organic Conductors DOI
Siew Ting Melissa Tan, Aristide Gumyusenge, Tyler J. Quill

и другие.

Advanced Materials, Год журнала: 2022, Номер 34(21)

Опубликована: Апрель 18, 2022

Organic mixed ionic-electronic conductors (OMIECs) have gained recent interest and rapid development due to their versatility in diverse applications ranging from sensing, actuation computation energy harvesting/storage, information transfer. Their multifunctional properties arise ability simultaneously participate redox reactions as well modulation of ionic electronic charge density throughout the bulk material. Most importantly, access states with deep through a large extent its physical volume material enables OMIEC-based devices display exciting new characteristics opens up degrees freedom device design. Leveraging infinite possibilities organic synthetic toolbox, this perspective highlights several chemical structural design approaches modify OMIECs' important such conductivity, color, modulus, etc. Additionally, for OMIECs respond external stimuli transduce signals myriad types outputs has accelerated smart systems. This further illustrates how various electrical, chemical, optical inputs fundamentally change dynamically these changes can be utilized applications.

Язык: Английский

Процитировано

56

The Effect of Glycol Side Chains on the Assembly and Microstructure of Conjugated Polymers DOI Creative Commons
Stefania Moro, Nicholas Siemons, Oscar Drury

и другие.

ACS Nano, Год журнала: 2022, Номер 16(12), С. 21303 - 21314

Опубликована: Дек. 14, 2022

Conjugated polymers with glycol-based chains, are emerging as a material class promising applications organic mixed ionic-electronic conductors, particularly in bioelectronics and thermoelectrics. However, little is still known about their microstructure the role of side chains determining intermolecular interactions polymer packing. Here, we use combination electrospray deposition scanning tunneling microscopy to determine prototypical glycolated conjugated (pgBTTT p(g2T-TT)) submonomer resolution. Molecular dynamics simulations same surface-adsorbed exhibit an excellent agreement experimental images, allowing us extend characterization atomic scale. Our results prove that, similarly alkylated counterparts, assemble through interdigitation although significant differences found conformation interaction patterns. A model proposed that identifies driving force for assembly tendency adopt free analogues, i.e., polyethylene glycol, alkyl or ethylene glycol respectively. For both classes polymers, it also demonstrated backbone determined higher degree by between rather than torsional potential energy. The generalization these findings from two-dimensional (2D) monolayers three-dimensional thin films discussed, together opportunity this type 2D study gain so far inaccessible, subnm-scale information on polymers.

Язык: Английский

Процитировано

48

Molecular-Scale Imaging Enables Direct Visualization of Molecular Defects and Chain Structure of Conjugated Polymers DOI Creative Commons
Stefania Moro, Simon E. F. Spencer, Daniel W. Lester

и другие.

ACS Nano, Год журнала: 2024, Номер 18(18), С. 11655 - 11664

Опубликована: Апрель 23, 2024

Conjugated polymers have become materials of choice for applications ranging from flexible optoelectronics to neuromorphic computing, but their polydispersity and tendency aggregate pose severe challenges precise characterization. Here, the combination vacuum electrospray deposition (ESD) with scanning tunneling microscopy (STM) is used acquire, within same experiment, assembly patterns, full mass distributions, exact sequencing, quantification polymerization defects. In a first step, ESD-STM results are successfully benchmarked against NMR low molecular polymers, where this technique still applicable. Then, it shown that capable reaching beyond its limits by characterizing, accuracy, samples inaccessible NMR. Finally, recalibration procedure proposed size exclusion chromatography (SEC) using as reference. The distinctiveness molecular-scale information obtained highlights role crucial characterization conjugated polymers.

Язык: Английский

Процитировано

10

The Role of Side Chains and Hydration on Mixed Charge Transport in n‐Type Polymer Films DOI Creative Commons
Jokūbas Surgailis, Lucas Q. Flagg, Lee J. Richter

и другие.

Advanced Materials, Год журнала: 2024, Номер unknown

Опубликована: Март 30, 2024

Abstract Introducing ethylene glycol (EG) side chains to a conjugated polymer backbone is well‐established synthetic strategy for designing organic mixed ion‐electron conductors (OMIECs). However, the impact that film swelling has on conduction properties yet be scoped, particularly electron‐transporting ( n ‐type) OMIECs. Here, authors investigate effect of length branched EG charge transport ‐type OMIECs based naphthalene‐1,4,5,8‐tetracarboxylic‐diimide‐bithiophene backbone. Atomic force microscopy (AFM), grazing‐incidence wide‐angle X‐ray scattering (GIWAXS), and scanning tunneling (STM) are used establish similarities between common‐backbone films in dry conditions. Electrochemical quartz crystal microbalance with dissipation monitoring (EQCM‐D) situ GIWAXS measurements reveal stark changes microstructure during electrochemical doping, depending chain length. It found even loss crystallite content upon contact aqueous electrolyte, can effectively charges it rather high water harms electronic interconnectivity within OMIEC films. These results highlight importance controlling uptake impede devices.

Язык: Английский

Процитировано

9

Perpendicular crossing chains enable high mobility in a noncrystalline conjugated polymer DOI Creative Commons
Jack F. Coker, Stefania Moro, Anders S. Gertsen

и другие.

Proceedings of the National Academy of Sciences, Год журнала: 2024, Номер 121(37)

Опубликована: Сен. 3, 2024

The nature of interchain π-system contacts, and their relationship to hole transport, are elucidated for the high-mobility, noncrystalline conjugated polymer C16-IDTBT by application scanning tunneling microscopy, molecular dynamics, quantum chemical calculations. microstructure is shown favor an unusual packing motif in which paired chains cross-over one another at near-perpendicular angles. By linking mesoscale microstructural features, revealed coarse-grained dynamics previous studies, performing simulations charge it demonstrated that high mobility can be explained promotion a highly interconnected transport network, stemming from adoption perpendicular contacts nanoscale, combination with fast intrachain transport.

Язык: Английский

Процитировано

8

Using Molecular Structure to Tune Intrachain and Interchain Charge Transport in Indacenodithiophene-Based Copolymers DOI
Garrett LeCroy, Raja Ghosh, Parker J. W. Sommerville

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(31), С. 21778 - 21790

Опубликована: Июль 26, 2024

In this work, we compare two structurally near-amorphous rigid-rod polymers─poly(indacenodithiophene-

Язык: Английский

Процитировано

7

Microstructural Model of Indacenodithiophene-co-benzothiadiazole Polymer: π-Crossing Interactions and Their Potential Impact on Charge Transport DOI Creative Commons
Hesam Makki, Colm Burke, Alessandro Troisi

и другие.

The Journal of Physical Chemistry Letters, Год журнала: 2023, Номер 14(39), С. 8867 - 8873

Опубликована: Сен. 27, 2023

Morphological and electronic properties of indacenodithiophene-co-benzothiadiazole (IDTBT) copolymer with varying molecular weights are calculated through combined dynamics (MD) quantum chemical (QC) methods. Our study focuses on the polymer chain arrangements, interchain connectivity pathways, interplay between morphological structure IDTBT. models, which verified against GIWAXS measurements, show a considerable number BT-BT π-π interactions (preferential) perpendicular local orientation chains due to steric hindrance bulky side around IDT. Although our models predict noncrystalline for IDTBT, (interchain) crossing points degree short-range order in spatial arrangement most likely result mesh-like provide efficient pathways charge transport.

Язык: Английский

Процитировано

14

On the Importance of Chemical Precision in Organic Electronics: Fullerene Intercalation in Perfectly Alternating Conjugated Polymers DOI Creative Commons
Jochen Vanderspikken, Zhen Liu, Xiaocui Wu

и другие.

Advanced Functional Materials, Год журнала: 2023, Номер 33(52)

Опубликована: Сен. 10, 2023

Abstract The true structure of alternating conjugated polymers—the state‐of‐the‐art materials for many organic electronics—often deviates from the idealized picture. Homocoupling defects are in fact inherent to widely used cross‐coupling polymerization methods. Nevertheless, polymers still perform excellently envisaged applications, which raises question if one should really care about these imperfections. This article looks at relevance chemical precision (and lack thereof) covering entire spectrum molecular scale, micro and mesostructure, up device level. different types errors alkoxylated variant benchmark (semi)crystalline polymer poly[2,5‐bis(3‐tetradecylthiophen‐2‐yl)thieno[3,2‐ b ]thiophene (PBTTT) identified, visualized, quantified a general strategy avoid homocoupling is introduced. Through combination experiments supported by simulations, it shown that coupling hinder fullerene intercalation limit performance as compared homocoupling‐free analog. clearly demonstrates structural do matter be generally avoided, particular when geometrical regularity essential. These insights likely go beyond specific PBTTT derivatives studied here wider electronics field.

Язык: Английский

Процитировано

13