New n-Type solution processable all conjugated polymer network: synthesis, optoelectronic characterization, and application in organic solar cells

H. Bildirir; D. Di Carlo Rasi; M.M. Wienk; R.A.J. Janssen; A. Avgeropoulos; V.G. Gregoriou; S. Allard; U. Scherf; C.L. Chochos

doi:10.1002/marc.201700629

New n-Type solution processable all conjugated polymer network: synthesis, optoelectronic characterization, and application in organic solar cells

H. Bildirir, D. Di Carlo Rasi, M.M. Wienk, R.A.J. Janssen, A. Avgeropoulos, V.G. Gregoriou, S. Allard, U. Scherf, C.L. Chochos

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The efficient synthesis of a new solution-processable n-type conjugated polymer network (PNT1) is reported through palladium-catalyzed Stille cross-coupling reaction conditions following the A₃ + B₂ synthetic approach. A benzo[1,2-b:3,4-b′:5,6-b″]trithiophene derivative is used as the A₃ knot and an alkyl functionalized naphthalenediimide is utilized as the B₂ linker. The thermal, optical, and electrochemical properties are examined in detail, showing high thermal stability, absorbance in the visible part of the solar spectrum, and reversible reduction characteristics similar to those of the fullerene derivative [6,6]-phenyl-C₇₁-butyric acid methyl ester (PC₇₁BM). PNT1 is employed as the electron acceptor in solution-processed bulk heterojunction organic solar cells, demonstrating the potential of this new type of materials for optoelectronic applications.

Originele taal-2	Engels
Artikelnummer	1700629
Pagina's (van-tot)	1-7
Tijdschrift	Macromolecular Rapid Communications
Volume	39
Nummer van het tijdschrift	5
DOI's	https://doi.org/10.1002/marc.201700629
Status	Gepubliceerd - 1 mrt. 2018

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Dr. H. Bildirir, Dr. V. G. Gregoriou, Dr. C. L. Chochos Advent Technologies SA Patras Science Park Stadiou Street, Platani-Rio, 26504 Patra, Greece E-mail: [email protected], [email protected] D. Di Carlo Rasi, Dr. M. M. Wienk, Prof. R. A. J. Janssen Molecular Materials and Nanosystems Institute for Complex Molecular Systems Eindhoven University of Technology P. O. Box 513, 5600 MB Eindhoven, The Netherlands Dr. M. M. Wienk, Prof. R. A. J. Janssen Dutch Institute for Fundamental Energy Research De Zaale, 20 5612 AJ Eindhoven, The Netherlands Prof. A. Avgeropoulos, Dr. C. L. Chochos Department of Materials Science Engineering University of Ioannina Ioannina 45110, Greece Dr. V. G. Gregoriou National Hellenic Research Foundation (NHRF) 48 Vassileos Constantinou Avenue Athens 11635, Greece Dr. S. Allard, Prof. U. Scherf Macromolecular Chemistry Group (buwmakro) and Institute for Polymer Technology Bergische Universität Wuppertal Gaußstraße 20, D-42119 Wuppertal, Germany The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/marc.201700629. This project received funding from the European Community’s Seventh Framework Programm (FP7/2007-2013) under the Grant Agreement No. 607585 project OSNIRO. The authors thank Dr. Alex Palma-Cando from Bergische Universität Wuppertal for the discussions on CV measurements.

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Bildirir, H., Di Carlo Rasi, D., Wienk, M. M., Janssen, R. A. J., Avgeropoulos, A., Gregoriou, V. G., Allard, S., Scherf, U., & Chochos, C. L. (2018). New n-Type solution processable all conjugated polymer network: synthesis, optoelectronic characterization, and application in organic solar cells. Macromolecular Rapid Communications, 39(5), 1-7. Artikel 1700629. https://doi.org/10.1002/marc.201700629

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title = "New n-Type solution processable all conjugated polymer network: synthesis, optoelectronic characterization, and application in organic solar cells",

abstract = "The efficient synthesis of a new solution-processable n-type conjugated polymer network (PNT1) is reported through palladium-catalyzed Stille cross-coupling reaction conditions following the A3 + B2 synthetic approach. A benzo[1,2-b:3,4-b′:5,6-b″]trithiophene derivative is used as the A3 knot and an alkyl functionalized naphthalenediimide is utilized as the B2 linker. The thermal, optical, and electrochemical properties are examined in detail, showing high thermal stability, absorbance in the visible part of the solar spectrum, and reversible reduction characteristics similar to those of the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). PNT1 is employed as the electron acceptor in solution-processed bulk heterojunction organic solar cells, demonstrating the potential of this new type of materials for optoelectronic applications.",

keywords = "conjugated polymers, donor–acceptor, low bandgap, near infrared, organic photovoltaics, Electric Power Supplies, Temperature, Models, Chemical, Polymers/chemical synthesis, Solar Energy, Light, Solutions/chemistry, Microscopy, Atomic Force, Molecular Structure, Naphthalenes/chemistry, Spectrophotometry, Thiophenes/chemistry, Imides/chemistry",

author = "H. Bildirir and {Di Carlo Rasi}, D. and M.M. Wienk and R.A.J. Janssen and A. Avgeropoulos and V.G. Gregoriou and S. Allard and U. Scherf and C.L. Chochos",

year = "2018",

month = mar,

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doi = "10.1002/marc.201700629",

language = "English",

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journal = "Macromolecular Rapid Communications",

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Bildirir, H, Di Carlo Rasi, D, Wienk, MM , Janssen, RAJ, Avgeropoulos, A, Gregoriou, VG, Allard, S, Scherf, U & Chochos, CL 2018, 'New n-Type solution processable all conjugated polymer network: synthesis, optoelectronic characterization, and application in organic solar cells', Macromolecular Rapid Communications, vol. 39, nr. 5, 1700629, blz. 1-7. https://doi.org/10.1002/marc.201700629

New n-Type solution processable all conjugated polymer network: synthesis, optoelectronic characterization, and application in organic solar cells. / Bildirir, H.; Di Carlo Rasi, D.; Wienk, M.M. et al.
In: Macromolecular Rapid Communications, Vol. 39, Nr. 5, 1700629, 01.03.2018, blz. 1-7.

Onderzoeksoutput: Bijdrage aan tijdschrift › Tijdschriftartikel › Academic › peer review

TY - JOUR

T1 - New n-Type solution processable all conjugated polymer network

T2 - synthesis, optoelectronic characterization, and application in organic solar cells

AU - Bildirir, H.

AU - Di Carlo Rasi, D.

AU - Wienk, M.M.

AU - Janssen, R.A.J.

AU - Avgeropoulos, A.

AU - Gregoriou, V.G.

AU - Allard, S.

AU - Scherf, U.

AU - Chochos, C.L.

PY - 2018/3/1

Y1 - 2018/3/1

N2 - The efficient synthesis of a new solution-processable n-type conjugated polymer network (PNT1) is reported through palladium-catalyzed Stille cross-coupling reaction conditions following the A3 + B2 synthetic approach. A benzo[1,2-b:3,4-b′:5,6-b″]trithiophene derivative is used as the A3 knot and an alkyl functionalized naphthalenediimide is utilized as the B2 linker. The thermal, optical, and electrochemical properties are examined in detail, showing high thermal stability, absorbance in the visible part of the solar spectrum, and reversible reduction characteristics similar to those of the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). PNT1 is employed as the electron acceptor in solution-processed bulk heterojunction organic solar cells, demonstrating the potential of this new type of materials for optoelectronic applications.

AB - The efficient synthesis of a new solution-processable n-type conjugated polymer network (PNT1) is reported through palladium-catalyzed Stille cross-coupling reaction conditions following the A3 + B2 synthetic approach. A benzo[1,2-b:3,4-b′:5,6-b″]trithiophene derivative is used as the A3 knot and an alkyl functionalized naphthalenediimide is utilized as the B2 linker. The thermal, optical, and electrochemical properties are examined in detail, showing high thermal stability, absorbance in the visible part of the solar spectrum, and reversible reduction characteristics similar to those of the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). PNT1 is employed as the electron acceptor in solution-processed bulk heterojunction organic solar cells, demonstrating the potential of this new type of materials for optoelectronic applications.

KW - conjugated polymers

KW - donor–acceptor

KW - low bandgap

KW - near infrared

KW - organic photovoltaics

KW - Electric Power Supplies

KW - Temperature

KW - Models, Chemical

KW - Polymers/chemical synthesis

KW - Solar Energy

KW - Light

KW - Solutions/chemistry

KW - Microscopy, Atomic Force

KW - Molecular Structure

KW - Naphthalenes/chemistry

KW - Spectrophotometry

KW - Thiophenes/chemistry

KW - Imides/chemistry

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U2 - 10.1002/marc.201700629

DO - 10.1002/marc.201700629

M3 - Article

C2 - 29251388

AN - SCOPUS:85038100186

SN - 1022-1336

VL - 39

SP - 1

EP - 7

JO - Macromolecular Rapid Communications

JF - Macromolecular Rapid Communications

IS - 5

M1 - 1700629

ER -

New n-Type solution processable all conjugated polymer network: synthesis, optoelectronic characterization, and application in organic solar cells

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