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A Super Electron Deficient Polymer

Synfacts, 2016, 12, 0357-0357.
10.1039/c7tc01680h

The authors report the synthesis of a thiophene-S,S-dioxidized indophenine-containing conjugated polymer PIDTOTT. This polymer exhibits unipolar n-type semiconductor characteristics with exceptionally high electron mobility (up to 0.14 cm2V–1s–1).

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Recent Publications

Article

A small bandgap (3E,7E)-3,7-bis(2-oxoindolin-3-ylidene)benzo[1,2-b:4,5-b’]difuran-2,6(3H,7H)-dione (IBDF) based polymer semiconductor for near-infrared organic phototransistors

Y. He, J. Quinn, D. Hou, J. H. L. Ngai and Y. Li, J. Mater. Chem. C, 2017, #, #-#.
10.1039/c7tc03584e

A (3E,7E)-3,7-bis(2-oxoindolin-3-ylidene)benzo[1,2-b:4,5-b’]difuran-2,6(3H,7H)-dione (IBDF)-based small bandgap donor-acceptor (D-A) polymer (PIBDFBTO-HH) was synthesized, which contains a strategically chosen solubilizing electron-rich building block, 3,3'-bis(dodecyloxy)-2,2'-bithiophene (BTO) as a donor. PIBDFBTO-HH has a very small band gap of 0.95 eV, absorbing up to 1700 nm in the near-infrared (NIR) region, which enables its application in NIR photodetection. This polymer exhibits efficient ambipolar charge transport properties with balanced hole and electron mobilities of up to 0.16 cm2 V-1 s-1 and 0.14 cm2 V-1 s-1, respectively, in organic thin film transistors (OTFTs) in the absence of light. In the p-channel operation regime, the organic phototransistor (OPT) devices based on PIBDFBTO-HH demonstrated photosensitivities (P) of 130 and 40 under the illumination of 850 nm and 940 nm LED light sources, respectively. The photoresponsivity (R) under the 940 nm LED reached 450 mA W-1. On the contrary, in the n-channel operation regime, a negative photoresponse, namely a decrease in the drain current, was observed, which is accounted for the increased number of trapped electrons that offset the applied gate bias.

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Article

New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics

T. Bura, S. Beaupré, O. A. Ibraikulov, M.-A. Légaré, J. Quinn, P. Lévêque, T. Heiser, Y. Li, N. Leclerc and M. Leclerc, Macromolecules, 2017, 50, 7080-7090.
10.1021/acs.macromol.7b01198

Diketopyrrolopyrrole (DPP) derivatives are among the most efficient materials studied for both polymer solar cells (PSCs) and organic field-effect transistors (OFETs) applications. We report here the synthesis of new fluorinated dithienyldiketopyrrolopyrrole (fDT-DPP) monomers suitable for direct heteroarylation polymerization. fDT-DPP copolymers were then prepared to probe the effect of the fluorination. It was found that they feature deeper HOMO energy levels and smaller bandgaps than their non-fluorinated analogues. Moreover, some fDT-DPP copolymers show ambipolar behavior when tested in OFETs. For example, P2 shows hole mobility up to 0.8 cm2 V–1 s–1 and electron mobility up to 0.5 cm2 V–1 s–1. Inverted PSCs with power conversion efficiency (PCE) up to 7.5% were also obtained for P5. These results reported here (OFETs and PSCs) confirm that the fluorination of dithienyl-DPP moieties improves the performance of organic electronics devices. This study is also evidencing the strength of the direct heteroarylation polymerization and fDT-DPP as a new class of conjugated polymers.

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Communication

Ultrafast photoresponse organic phototransistors based on pyrimido[4,5-g]quinazoline-4,9-dione polymer

J. T. E. Quinn, F. Haider, H. Patel, D. A. Khan, Z. Y. Wang and Y. Li, J. Mater. Chem. C, 2017, 5, 8742-8748.
10.1039/c7tc03023a

We report the photoresponse characteristics of a pyrimido[4,5-g]quinazoline-4,9-dione (PQ) based polymer, PPQ2T-BT-24, which served as an active channel layer in organic phototransistors (OPTs). OPTs using this polymer showed very short rise time of 3 ms and fall time of 59 ms, photoresponsivity (R) of 0.24 and external quantum efficiency (EQE) of 50%. When PC61BM was incorporated into PPQ2T-BT-24, a significantly shortened fall time of 8 ms along with a much-improved rise time of 1 ms were realized. These response times are among the best values reported for OPTs. The R and EQE of the devices using this polymer blend also increased to 0.88 A W−1 and 189%, respectively.

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Review

Recent progress in the development of n-type organic semiconductors for organic field effect transistors

J. T. E. Quinn, J. Zhu, X. Li, J. Wang and Y. Li, J. Mater. Chem. C, 2017, 5, 8654-8681.
10.1039/c7tc01680h

This review highlights recent major progress in the development of organic semiconductors as electron transport n-channel materials in organic field effect transistors (OFETs). Three types of materials are discussed: (1) small molecules, (2) polymers, and (3) n-doped small molecules and polymers. Much effort has been made in the modification of known building blocks, development of novel building blocks, and optimization of materials processing and device structures. These efforts have resulted in the achievement of record high electron mobilities for both small molecules (12.6 cm2 V−1 s−1) and polymers (14.9 cm2 V−1 s−1), which are approaching the highest hole mobilities achieved by p-type small molecules and polymers so far. In addition, n-doping of ambipolar and p-type organic semiconductors has proven to be an efficient approach to obtaining a greater number of n-type organic semiconductors. However, it is found that n-type organic semiconductors, in general, still lag behind p-type organic semiconductors in terms of carrier mobility and air stability. Further exploration of new building blocks for making novel materials and optimization of processing conditions and device structures are needed to improve the performance, particularly air stability.

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Previous Publications

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Article

New 3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) (EBI)-based small molecule semiconductors for organic solar cells

M. Le Borgne, J. Quinn, J. Martin, N. Stingelin, Y. Li and G. Wantz, J. Mater. Chem. C, 2017, 5, 5143-5153.

10.1039/c7tc00711f

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Article

An aromatic amine-containing polymer as an additive to ambipolar polymer semiconductor realizing unipolar n-type charge transport

Y. He, J. T. E. Quinn, S. Lee, G. Y. Wang, X. Li, J. Wang and Y. Li, Org. Electron., 2017, 49, 406-414.

10.1016/j.orgel.2017.07.016

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Article

Regioisomerism of an alkyl-substituted bithiophene comonomer in (3E,8E)-3,8-bis(2-oxoindolin-3-ylidene)naphtho-[1,2-b:5,6-b′]difuran-2,7(3H,8H)-dione (INDF)-based D–A polymers for organic thin film transistors

J. T. E. Quinn, C. Guo, F. Haider, H. Patel, D. A. Khan and Y. Li, J. Mater. Chem. C, 2017, 5, 5902-5909.

10.1039/c7tc01204g

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Communication

Converting a Semiconducting Polymer from Ambipolar into n-Type Dominant by Amine End-Capping

J. Quinn, H. Patel, F. Haider, D. A. Khan and Y. Li, ChemElectroChem, 2017, 4, 256-260.

10.1002/celc.201600628

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Edge Article

Direct heteroarylation polymerization: guidelines for defect-free conjugated polymers

T. Bura, S. Beaupré, M.-A. Légaré, J. Quinn, E. Rochette, J. T. Blaskovits, F.-G. Fontaine, A. Pron, Y. Li and M. Leclerc, Chem. Sci., 2017, 8, 3913-3925.

10.1039/c7sc00589j

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Article

A Study of the Degree of Fluorination in Regioregular Poly(3-hexylthiophene)

J. T. Blaskovits, T. Bura, S. Beaupré, S. A. Lopez, C. Roy, J. de Goes Soares, A. Oh, J. Quinn, Y. Li, A. Aspuru-Guzik and M. Leclerc, Macromolecules, 2017, 50, 162-174.

10.1021/acs.macromol.6b02365

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Article

Synthesis, characterization, and air stability study of pyrimido[4,5-g]quinazoline-4,9-dione-based polymers for organic thin film transistors

J. Quinn, Y. He, D. A. Khan, J. Rasmussen, H. Patel, F. Haider, W. Kapadia and Y. Li, RSC Adv., 2016, 6, 78477-78485.

10.1039/c6ra17595c

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Article

Pyrazino[2,3-g]quinoxaline-2,7-dione based π-conjugated polymers with affinity towards acids and semiconductor performance in organic thin film transistors

J. Quinn, C. Guo, L. Ko, B. Sun, Y. He and Y. Li, RSC Adv., 2016, 6, 22043-22051.

10.1039/c5ra26227e

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Article

Synthesis and properties of a novel narrow band gap oligomeric diketopyrrolopyrrole-based organic semiconductor

M. Le Borgne, J. Quinn, J. Martín, N. Stingelin, G. Wantz and Y. Li, Dyes Pigm., 2016, 131, 160-167.

10.1016/j.dyepig.2016.04.002

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Article

3,7-Bis((E)-2-oxoindolin-3-ylidene)-3,7-dihydrobenzo[1,2-b:4,5-b′]dithiophene-2,6-dione (IBDT) based polymer with balanced ambipolar charge transport performance

Y. He, J. Quinn, Y. Deng and Y. Li, Org. Electron., 2016, 35, 41-46.

10.1016/j.orgel.2016.05.003

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Article

A fluorene-fused triphenodioxazine (FTPDO) based polymer with remarkable thermal stability and significantly enhanced charge transport performance in air

L. Guo, J. Quinn, J. Wang, C. Guo, X. Li, J. Wang and Y. Li, Dyes Pigm., 2016, 132, 329-335.

10.1016/j.dyepig.2016.05.011

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Article

Dramatically different charge transport properties of bisthienyl diketopyrrolopyrrole-bithiazole copolymers synthesized via two direct (hetero)arylation polymerization routes

C. Guo, J. Quinn, B. Sun and Y. Li, Polym. Chem., 2016, 7, 4515-4524.

10.1039/c6py00762g

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Article

Thiophene-S,S-dioxidized indophenines as high performance n-type organic semiconductors for thin film transistors

Y. Deng, B. Sun, J. Quinn, Y. He, J. Ellard, C. Guo and Y. Li, RSC Adv., 2016, 6, 45410-45418.

10.1039/c6ra06316k

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Communication

Thiophene-S,S-dioxidized Indophenine: A Quinoid-Type Building Block with High Electron Affinity for Constructing n-Type Polymer Semiconductors with Narrow Band Gaps

Y. Deng, B. Sun, Y. He, J. Quinn, C. Guo and Y. Li, Angew. Chem., Int. Ed. Engl., 2016, 55, 3459-3462.

10.1002/anie.201508781

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Article

Thiophene-S,S-dioxidized indophenine (IDTO) based donor–acceptor polymers for n-channel organic thin film transistors

Y. Deng, J. Quinn, B. Sun, Y. He, J. Ellard and Y. Li, RSC Adv., 2016, 6, 34849-34854.

10.1039/c6ra03221d

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Article

Surface modification of polydimethylsiloxane elastomer for stable hydrophilicity, optical transparency and film lubrication

H. Shahsavan, J. Quinn, J. d’Eon and B. Zhao, Colloids Surf., A, 2015, 482, 267-275.

10.1016/j.colsurfa.2015.05.024

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Article

Pyrimido[4,5-g]quinazoline-4,9-dione as a new building block for constructing polymer semiconductors with high sensitivity to acids and hole transport performance in organic thin film transistors

J. Quinn, C. Guo, B. Sun, A. Chan, Y. He, E. Jin and Y. Li, J. Mater. Chem. C, 2015, 3, 11937-11944.

10.1039/c5tc02472b

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Article

New synthetic route to pyrimido[4,5-g]quinazoline-4,9-diones

J. Quinn, E. Jin and Y. Li, Tetrahedron Lett., 2015, 56, 2280-2282.

10.1016/j.tetlet.2015.03.085

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Communication

(3E,7E)-3,7-Bis(2-oxoindolin-3-ylidene)-5,7-dihydropyrrolo[2,3-f]indole-2,6(1H,3H )-dione based polymers for ambipolar organic thin film transistors

Y. He, C. Guo, B. Sun, J. Quinn and Y. Li, Chem. Commun. (Cambridge, U. K.), 2015, 51, 8093-8096.

10.1039/c5cc01021g

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Article

Branched alkyl ester side chains rendering large polycyclic (3E,7E)-3,7-bis(2-oxoindolin-3-ylidene)benzo[1,2-b:4,5-b′]difuran-2,6(3H,7H)-dione (IBDF) based donor–acceptor polymers solution-processability for organic thin film transistors

Y. He, C. Guo, B. Sun, J. Quinn and Y. Li, Polym. Chem., 2015, 6, 6689-6697.

10.1039/c5py00782h

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Communication

(3E,8E)-3,8-Bis(2-oxoindolin-3-ylidene)naphtho-[1,2-b:5,6-b']difuran-2,7(3H,8H)-d ione (INDF) based polymers for organic thin-film transistors with highly balanced ambipolar charge transport characteristics

Y. Deng, B. Sun, Y. He, J. Quinn, C. Guo and Y. Li, Chem. Commun. 2015, 51, 13515-13518.

10.1039/c5cc03917g

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Article

Regioisomeric control of charge transport polarity for indigo-based polymers

C. Guo, J. Quinn, B. Sun and Y. Li, Polym. Chem., 2015, 6, 6998-7004.

10.1039/c5py00821b

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Article

An indigo-based polymer bearing thermocleavable side chains for n-type organic thin film transistors

C. Guo, J. Quinn, B. Sun and Y. Li, J. Mater. Chem. C, 2015, 3, 5226-5232.

10.1039/c5tc00512d

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Article

Synthesis and properties of indigo based donor–acceptor conjugated polymers

C. Guo, B. Sun, J. Quinn, Z. Yan and Y. Li, J. Mater. Chem. C, 2014, 2, 4289-4296.

10.1039/c3tc32276a