Direct arylation polymerization of asymmetric push–pull aryl halides

You, Lijun; Chaudhry, Saadia T.; Zhao, Yan; Liu, Junchen; Zhao, Xikang; He, Jiazhi; Mei, Jianguo

doi:10.1039/c7py00237h

Cited by 14 publications

(10 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, the mobility of P107 was only 3.02 × 10 −3 cm 2 V −1 s −1 . [66] Wan and co-workers synthesized homopolymer P108 of M21 using one-pot polymerization method. [63] The weak steric hindrance between the adjacent units contributed to good polymer planarity and crystallinity.…”

Section: Homopolymersmentioning

confidence: 99%

“…In this report, the polymerization precursor was functionalized by both CBr bond and CH bond. [ 66 ] Although the three coupling methods are currently the main synthetic methods for isoindigo‐derived polymers, they still have some drawbacks. For example, Stille couplings involve highly toxic organotin reagents.…”

Section: Synthetic Tactics Of Isoindigo‐derived Monomers and Polymersmentioning

confidence: 99%

“…By contrast, Mei and co‐workers synthesized P107 using only M2 as the precursor. [ 66 ] The difference in electronic structures of the phenyl ring and the thienyl ring makes M2 an intramolecular donor–acceptor structure, thereby making its feasible to directly prepare D–A homopolymer. However, the mobility of P107 was only 3.02 × 10 −3 cm 2 V −1 s −1 .…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

See 2 more Smart Citations

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

Wei

Zhang

2021

Adv Funct Materials

View full text Add to dashboard Cite

(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

show abstract

Section: Homopolymersmentioning

confidence: 99%

Section: Synthetic Tactics Of Isoindigo‐derived Monomers and Polymersmentioning

confidence: 99%

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

See 1 more Smart Citation

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

Wei

Zhang

2021

Adv Funct Materials

View full text Add to dashboard Cite

show abstract

“…In this regard, the most studied and promising are π-conjugated polymer structures based on sulfur, oxygen, nitrogen, and selenium heterocyclic compounds [62,63]. One of the systems for creating OFET devices is the isoindigo platform [64][65][66][67][68]. Scheme 22 shows polymeric structures with the best mobility values among isoindigo derivatives that are known to date.…”

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.

View full text Add to dashboard Cite

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.

show abstract

“…Therefore, the self‐condensation‐type DArP is more attractive than DArP for the AA‐BB system from a practical point of view. However, the synthesis of low‐band‐gap conjugated polymers through self‐condensation‐type DArP is far less developed than that through DArP on the AA‐BB system . We previously reported the self‐condensation‐type direct arylation synthesis of a naphthalene bisimide (NBI)‐dithiophene alternating copolymer from a newly designed asymmetric NBI‐based D‐A monomer.…”

Section: Introductionmentioning

confidence: 99%

Direct arylation synthesis of thienoisoindigo‐based low‐band‐gap polymer from asymmetric donor–acceptor monomer

Nakabayashi

Fukuzawa

Fujita

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

View full text Add to dashboard Cite

Thienoisoindigo (TIG) moiety has been paid numerous attentions as an excellent acceptor building block in low‐band‐gap polymers. Herein, a new TIG‐dithiophene alternating copolymer (PTIG2T) was successfully synthesized from an asymmetric TIG‐based donor–acceptor (D‐A) monomer via the self‐condensation‐type direct arylation polymerization. PTIG2T exhibited the light absorption over 1000 nm owing to the intramolecular charge transfer in the thin film state, which corresponded to an optical band gap of 1.24 eV. The HOMO and LUMO levels of PTIG2T were determined to be −5.08 and −3.60 eV, respectively. Furthermore, the organic photovoltaic (OPV) with a PTIG2T/PC61BM active layer achieved a power conversion efficiency (PCE) of 3.19%, which is one of the highest PEC achieved by OPVs with TIG‐based materials. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 430–436

show abstract

Direct arylation polymerization of asymmetric push–pull aryl halides

Abstract: Recently, direct arylation polymerization (DArP) has emerged as a greener polymerization method for donor–acceptor (D–A) type conjugated polymers.

Cited by 14 publications

References 21 publications

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

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

Direct arylation synthesis of thienoisoindigo‐based low‐band‐gap polymer from asymmetric donor–acceptor monomer

Contact Info

Product

Resources

About