The benzyl viologen radical cation: an effective n-dopant for poly(naphthalenediimide-bithiophene)

Tam, Teck Lip Dexter; Lin, Tingting; Omer, Mohamed I.; Wang, Xizu; Xu, Jianwei

doi:10.1039/d0ta06315k

Cited by 19 publications

(5 citation statements)

References 56 publications

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“…DQ was found to be effective for doping in ternary blends for bulk heterojunction OPV applications, leading to an improvement in OPV device efficiency . BV was proven to be a strong dopant in both OFET and thermoelectric devices, overcoming stability issues related to doping with TDAE, and contact resistance issues associated with DMBI and DPBI. , Certain electron-rich enamines exist in equilibrium with their corresponding carbenes (the Wanzlick equilibria). Depending on their structures, the dimeric form may readily convert into the corresponding N-heterocyclic carbene (NHC).…”

Section: Molecular Doping Of Organic Semiconductorsmentioning

confidence: 99%

Doping Approaches for Organic Semiconductors

et al. 2021

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Electronic doping in organic materials has remained an elusive concept for several decades. It drew considerable attention in the early days in the quest for organic materials with high electrical conductivity, paving the way for the pioneering work on pristine organic semiconductors (OSCs) and their eventual use in a plethora of applications. Despite this early trend, however, recent strides in the field of organic electronics have been made hand in hand with the development and use of dopants to the point that are now ubiquitous. Here, we give an overview of all important advances in the area of doping of organic semiconductors and their applications. We first review the relevant literature with particular focus on the physical processes involved, discussing established mechanisms but also newly proposed theories. We then continue with a comprehensive summary of the most widely studied dopants to date, placing particular emphasis on the chemical strategies toward the synthesis of molecules with improved functionality. The processing routes toward doped organic films and the important doping−processing−nanostructure relationships, are also discussed. We conclude the review by highlighting how doping can enhance the operating characteristics of various organic devices.

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Section: Molecular Doping Of Organic Semiconductorsmentioning

confidence: 99%

Doping Approaches for Organic Semiconductors

et al. 2021

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“…First, PNDIT2/IM-0.0 exhibited a single imide (O=C-N-C=O) peak from the NDI moiety at 400.2 eV (NDI-peak), which is well-matched with the results of the previous studies. [53][54][55] Meanwhile, after the integration of IM into NDI, PNDIT2/IM-0.3 showed an additional peak at 398.5 eV, associated with the C=N bonds of IM (IM-peak). [53,56,57] Afterward, when the PEI dopant was introduced, the IM-0.3/P-0.4 blend sample exhibited an enhanced intensity of the peak between 397 and 400 eV, where the IM-peak and PEI-peak (from the R-N-H bond of PEI) overlapped.…”

Section: Sensing Element Sensing Temperature [°C] Sensitivity [%] Lod...mentioning

confidence: 99%

High‐Performance, Flexible NO₂ Chemiresistors Achieved by Design of Imine‐Incorporated n‐Type Conjugated Polymers

et al. 2022

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Flexible and mechanically robust gas sensors are the key technologies for wearable and implantable electronics. Herein, the authors demonstrate the high-performance, flexible nitrogen dioxide (NO 2 ) chemiresistors using a series of n-type conjugated polymers (CPs: PNDIT2/IM-x) and a polymer dopant (poly(ethyleneimine), PEI). Imine double bonds (C = N) are incorporated into the backbones of the CPs with different imine contents (x) to facilitate strong and selective interactions with NO 2 . The PEI provides doping stability, enhanced electrical conductivity, and flexibility. As a result, the NO 2 sensors with PNDIT2/IM-0.1 and PEI (1:1 by weight ratio) exhibit outstanding sensing performances, such as excellent sensitivity (𝚫R/R b = 240% @ 1 ppm), ultralow detection limit (0.1 ppm), high selectivity (𝚫R/R b < 8% @ 1 ppm of interfering analytes), and high stability, thereby outperforming other state-of-the-art CP-based chemiresistors. Furthermore, the thin film of PNDIT2/IM-0.1 and PEI blend is stretchable and mechanically robust, providing excellent flexibility to the NO 2 sensors. Our study contributes to the rational design of high-performance flexible gas sensors.

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“…The HOMO value for r-BV 0 was derived from a cyclic voltammetry (CV) measurement vs. the standard hydrogen electrode (SHE), and by using the convention that the SHE electrode is offset by 4.44 eV from the vacuum level. 30 , 50 , 51 The HOMO and LUMO of Super Yellow were similarly determined from CV measurements, 52 while a major and generic electron trap level in organic semiconductors was identified and rationalized by Blom et al 47 , 49 A recent LEC study further suggest that the inclusion of the TMPE-OH ion transporter into the active material of our LEC devices can result in the formation of a significant concentration of additional electron traps 25 , but their exact energy level is currently unknown. Nevertheless, the presented electron-energy diagram implies that an electron transfer from the HOMO of r-BV 0 to the established electron-trap level of Super Yellow should be possible, as indicated by the arrow in Fig.…”

Section: Resultsmentioning

confidence: 99%

Chemical doping to control the in-situ formed doping structure in light-emitting electrochemical cells

Huseynova

Ràfols‐Ribé

Auroux

et al. 2023

Sci Rep

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The initial operation of a light-emitting electrochemical cell (LEC) constitutes the in-situ formation of a p–n junction doping structure in the active material by electrochemical doping. It has been firmly established that the spatial position of the emissive p–n junction in the interelectrode gap has a profound influence on the LEC performance because of exciton quenching and microcavity effects. Hence, practical strategies for a control of the position of the p–n junction in LEC devices are highly desired. Here, we introduce a “chemical pre-doping” approach for the rational shifting of the p–n junction for improved performance. Specifically, we demonstrate, by combined experiments and simulations, that the addition of a strong chemical reductant termed “reduced benzyl viologen” to a common active-material ink during LEC fabrication results in a filling of deep electron traps and an associated shifting of the emissive p–n junction from the center of the active material towards the positive anode. We finally demonstrate that this chemical pre-doping approach can improve the emission efficiency and stability of a common LEC device.

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The benzyl viologen radical cation: an effective n-dopant for poly(naphthalenediimide-bithiophene)

Abstract: n-Doping of poly(naphthalenediimide-bithiophene) was demonstrated using benzyl viologen radical cation.

Cited by 19 publications

References 56 publications

Doping Approaches for Organic Semiconductors

Doping Approaches for Organic Semiconductors

High‐Performance, Flexible NO₂ Chemiresistors Achieved by Design of Imine‐Incorporated n‐Type Conjugated Polymers

Chemical doping to control the in-situ formed doping structure in light-emitting electrochemical cells

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The benzyl viologen radical cation: an effective n-dopant for poly(naphthalenediimide-bithiophene)

Abstract: n-Doping of poly(naphthalenediimide-bithiophene) was demonstrated using benzyl viologen radical cation.

Cited by 19 publications

References 56 publications

Doping Approaches for Organic Semiconductors

Doping Approaches for Organic Semiconductors

High‐Performance, Flexible NO2 Chemiresistors Achieved by Design of Imine‐Incorporated n‐Type Conjugated Polymers

Chemical doping to control the in-situ formed doping structure in light-emitting electrochemical cells

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High‐Performance, Flexible NO₂ Chemiresistors Achieved by Design of Imine‐Incorporated n‐Type Conjugated Polymers