α,β-Unsubstituted meso-Positioning Thienyl BODIPY: A Promising Electron Deficient Building Block for the Development of Near Infrared (NIR) p-type Donor-Acceptor (D-A) Conjugated Polymers

Handle URI:
http://hdl.handle.net/10754/627232
Title:
α,β-Unsubstituted meso-Positioning Thienyl BODIPY: A Promising Electron Deficient Building Block for the Development of Near Infrared (NIR) p-type Donor-Acceptor (D-A) Conjugated Polymers
Authors:
Squeo, Benedetta; Gregoriou, Vasilis G.; Han, Yang; Palma-Cando, Alex; Allard, Sybille; Serpetzoglou, Efthymis; Konidakis, Ioannis; Stratakis, Emmanuel; Avgeropoulos, Apostolos; Anthopoulos, Thomas D. ( 0000-0002-0978-8813 ) ; Heeney, Martin; Scherf, Ullrich; Chochos, Christos L.
Abstract:
It is demonstrated that α,β-unsubstituted meso-positioning thienyl BODIPY is an electron deficient unit that leads to the development of ultra low optical band gap (Egopt < 1 eV) π-conjugated D-A quarterthiophene polymers. Furthermore, it is revealed that the optoelectronic, electrochemical and charge transporting properties of the resulting α,β-unsubstituted meso-positioning thienyl BODIPY quaterthiophene-based polymers are alkyl side chain positioning dependent. Tail-to-tail (TT) positioning of the alkyl side chains at the two central thiophenes of the quaterthiophene segment results to lower Egopt, higher energy levels and increased hole mobility as compared to head-to-head (HH) positioning. Finally, even though the synthesized polymers exhibit high electron affinity, higher even to that of the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM), they present only p-type behaviour in field effect transistors (FETs) independent to the alkyl side chain positioning.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Materials Science and Engineering Program; KAUST Solar Center (KSC)
Citation:
Squeo B, Gregoriou VG, Han Y, Palma-Cando A, Allard S, et al. (2018) α,β-Unsubstituted meso-Positioning Thienyl BODIPY: A Promising Electron Deficient Building Block for the Development of Near Infrared (NIR) p-type Donor-Acceptor (D-A) Conjugated Polymers. Journal of Materials Chemistry C. Available: http://dx.doi.org/10.1039/c7tc05900k.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Journal of Materials Chemistry C
Issue Date:
27-Feb-2018
DOI:
10.1039/c7tc05900k
Type:
Article
ISSN:
2050-7526; 2050-7534
Sponsors:
This project has received funding from the European Community’s Seventh Framework Programme (FP7/2007-2013) under the Grant Agreement n° 331389 project ECOCHEM, n° 607585 project OSNIRO and no 604603 project MatHero. The authors would like to thank Anke Helfer from BUW for the mass spectrometry measurements.
Additional Links:
http://pubs.rsc.org/en/Content/ArticleLanding/2018/TC/C7TC05900K#!divAbstract
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Materials Science and Engineering Program; KAUST Solar Center (KSC)

Full metadata record

DC FieldValue Language
dc.contributor.authorSqueo, Benedettaen
dc.contributor.authorGregoriou, Vasilis G.en
dc.contributor.authorHan, Yangen
dc.contributor.authorPalma-Cando, Alexen
dc.contributor.authorAllard, Sybilleen
dc.contributor.authorSerpetzoglou, Efthymisen
dc.contributor.authorKonidakis, Ioannisen
dc.contributor.authorStratakis, Emmanuelen
dc.contributor.authorAvgeropoulos, Apostolosen
dc.contributor.authorAnthopoulos, Thomas D.en
dc.contributor.authorHeeney, Martinen
dc.contributor.authorScherf, Ullrichen
dc.contributor.authorChochos, Christos L.en
dc.date.accessioned2018-03-06T06:50:09Z-
dc.date.available2018-03-06T06:50:09Z-
dc.date.issued2018-02-27en
dc.identifier.citationSqueo B, Gregoriou VG, Han Y, Palma-Cando A, Allard S, et al. (2018) α,β-Unsubstituted meso-Positioning Thienyl BODIPY: A Promising Electron Deficient Building Block for the Development of Near Infrared (NIR) p-type Donor-Acceptor (D-A) Conjugated Polymers. Journal of Materials Chemistry C. Available: http://dx.doi.org/10.1039/c7tc05900k.en
dc.identifier.issn2050-7526en
dc.identifier.issn2050-7534en
dc.identifier.doi10.1039/c7tc05900ken
dc.identifier.urihttp://hdl.handle.net/10754/627232-
dc.description.abstractIt is demonstrated that α,β-unsubstituted meso-positioning thienyl BODIPY is an electron deficient unit that leads to the development of ultra low optical band gap (Egopt < 1 eV) π-conjugated D-A quarterthiophene polymers. Furthermore, it is revealed that the optoelectronic, electrochemical and charge transporting properties of the resulting α,β-unsubstituted meso-positioning thienyl BODIPY quaterthiophene-based polymers are alkyl side chain positioning dependent. Tail-to-tail (TT) positioning of the alkyl side chains at the two central thiophenes of the quaterthiophene segment results to lower Egopt, higher energy levels and increased hole mobility as compared to head-to-head (HH) positioning. Finally, even though the synthesized polymers exhibit high electron affinity, higher even to that of the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM), they present only p-type behaviour in field effect transistors (FETs) independent to the alkyl side chain positioning.en
dc.description.sponsorshipThis project has received funding from the European Community’s Seventh Framework Programme (FP7/2007-2013) under the Grant Agreement n° 331389 project ECOCHEM, n° 607585 project OSNIRO and no 604603 project MatHero. The authors would like to thank Anke Helfer from BUW for the mass spectrometry measurements.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.relation.urlhttp://pubs.rsc.org/en/Content/ArticleLanding/2018/TC/C7TC05900K#!divAbstracten
dc.rightsArchived with thanks to Journal of Materials Chemistry Cen
dc.subjectconjugated polymersen
dc.subjectNear Infrared (NIR)en
dc.subjectBODIPYen
dc.subjectdyesen
dc.subjectpolythiophenesen
dc.titleα,β-Unsubstituted meso-Positioning Thienyl BODIPY: A Promising Electron Deficient Building Block for the Development of Near Infrared (NIR) p-type Donor-Acceptor (D-A) Conjugated Polymersen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentMaterials Science and Engineering Programen
dc.contributor.departmentKAUST Solar Center (KSC)en
dc.identifier.journalJournal of Materials Chemistry Cen
dc.eprint.versionPost-printen
dc.contributor.institutionAdvent Technologies SA, Patras Science Park, Stadiou Street, Platani-Rio, 26504, Patra, Greece.en
dc.contributor.institutionNational Hellenic Research Foundation (NHRF), 48 Vassileos Constantinou Avenue, Athens 11635, Greece.en
dc.contributor.institutionDepartment of Chemistry and Centre for Plastic Electronics, Imperial College London, Exhibition Road, South Kensington, London, SW7 2AY, UK.en
dc.contributor.institutionMacromolecular Chemistry Group (buwmakro) and Institute for Polymer Technology, Bergische Universität Wuppertal, Gaußstraße 20, D-42119 Wuppertal, Germany.en
dc.contributor.institutionInstitute of Electronic Structure and Laser, Foundation for Research and Technology – Hellas, P. O. Box 1527, Heraklion, Crete, Greeceen
dc.contributor.institutionDepartment of Materials Science Engineering, University of Ioannina, Ioannina 45110, Greece.en
dc.contributor.institutionDepartment of Physics and Centre for Plastic Electronics, Imperial College London, Exhibition Road, South Kensington, London, SW7 2AY, UK.en
kaust.authorAnthopoulos, Thomas D.en
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