Effects of Side Chain on High Temperature Operation Stability of Conjugated Polymers

Tran, Dung T.; Gumyusenge, Aristide; Luo, Xuyi; Roders, Michael; Yi, Zhengran; Ayzner, Alexander L.; Mei, Jianguo

doi:10.1021/acsapm.9b00999

Cited by 19 publications

(20 citation statements)

References 32 publications

(53 reference statements)

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“…Weakening of such interactions is known to lower the thermal stability of polymers. [40,41] To measure the glass transition temperature of the resulting polymer we have tried to employ conventional DSC. However, this technique has failed to detect the transition in a range of 25-400 °C.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Polymerization Kinetics of Novel Dicyanate Ester Based on Dimer of 4‐tert‐butylphenol

Galukhin

Nosov

Taimova

et al. 2021

Macro Chemistry & Physics

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A novel dicyanate ester, which constitutes the first member of the family of linear oligomers of 4‐tert‐butyl‐phenol, is synthesized as a part of the systematic study on the relation between the reactivity of cyanate esters and their structure. The synthesized monomer undergoes thermally stimulated polymerization in the melt. The kinetics of polymerization is studied by conventional and temperature‐modulated DSC. Detailed isoconversional analysis of the obtained kinetic data has revealed that the process rate is limited by a single reaction step of the auto‐catalytic nature. Thermal stability and glass transition temperature of polymerization product are characterized by means of thermogravimetry and fast scanning calorimetry.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Polymerization Kinetics of Novel Dicyanate Ester Based on Dimer of 4‐tert‐butylphenol

Galukhin

Nosov

Taimova

et al. 2021

Macro Chemistry & Physics

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“…Mei and co‐workers investigated the effect of polymer branching side chains (2‐octyldodecyl and 4‐decyltetradecyl for P1 and P3 , respectively) on device thermal stability. [ 83 ] P3 with longer side chains exhibited less alteration in charge mobility and threshold voltage at high temperature, because closer π–π stacking distance enabled better thermal stability. [ 83 ] For P11 and P12 with different carbosilane side chains, they displayed low tensile moduli of 0.43 and 0.27 GPa, respectively.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

“…[ 83 ] P3 with longer side chains exhibited less alteration in charge mobility and threshold voltage at high temperature, because closer π–π stacking distance enabled better thermal stability. [ 83 ] For P11 and P12 with different carbosilane side chains, they displayed low tensile moduli of 0.43 and 0.27 GPa, respectively. The decrease in the tensile modulus of P12 over P11 resulted from the decrease in volume fraction of rigid conjugated backbones.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

Zhang

2021

Adv Funct Materials

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(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

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“…According to the available data, the most studied polymeric isoindigos are dithienyl derivatives, in which two thiophene fragments can be linked to each other [74][75][76][77][78][79][80][81][82][83][84][85][86] or be separated by spacers of different structures [87][88][89][90][91]. Structures containing a 2,2'-dithienyl fragment can be divided into three types: 1) not containing substituents in the benzo and thienyl fragments; 2) containing fluorine atoms in the thienyl fragment; and 3) containing fluorine atoms in positions 7,7' and in thienyl fragments (Scheme 24).…”

Section: Isoindigo As the Basis For Organic Field-effect Transistors (Ofet)mentioning

confidence: 99%

Recent advances in the application of isoindigo derivatives in materials chemistry

Богданов¹,

Миронов²

2021

Beilstein J. Org. Chem.

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In this review, the data on the application of isoindigo derivatives in the chemistry of functional materials are analyzed and summarized. These bisheterocycles can be used in the creation of organic solar cells, sensors, lithium ion batteries as well as in OFET and OLED technologies. The potentials of the use of polymer structures based on isoindigo as photoactive component in the photoelectrochemical reduction of water, as matrix for MALDI spectrometry and in photothermal cancer therapy are also shown. Data published over the past 5 years, including works published at the beginning of 2021, are given.

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Effects of Side Chain on High Temperature Operation Stability of Conjugated Polymers

Cited by 19 publications

References 32 publications

Synthesis and Polymerization Kinetics of Novel Dicyanate Ester Based on Dimer of 4‐tert‐butylphenol

Synthesis and Polymerization Kinetics of Novel Dicyanate Ester Based on Dimer of 4‐tert‐butylphenol

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Recent advances in the application of isoindigo derivatives in materials chemistry

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