Development of an Electron-Transporting π-Conjugated Polymer Containing Fluorine-substituted Naphthobisthiadiazole

The development of new organic semiconductors for organic solar cell applications continues to be as an important subject. We recently developed fluorinated naphthobisthiadiazole (FNTz) for use as a new electron-accepting unit for nonfullerene acceptors. In this letter we report on the design and sy...

Full description

Saved in:
Bibliographic Details
Published inJournal of Photopolymer Science and Technology Vol. 32; no. 5; pp. 721 - 725
Main Authors Ie, Yutaka, Izuno, Kakeru, Moriyama, Taichi, Aso, Yoshio
Format Journal Article
LanguageEnglish
Published The Society of Photopolymer Science and Technology(SPST) 24.06.2019
Subjects
Acceptor
Fluorinated naphthobisthiadiazole
Organic semiconductors
Organic solar cell
Structure-property relationship
Online AccessGet full text

Cover

Abstract The development of new organic semiconductors for organic solar cell applications continues to be as an important subject. We recently developed fluorinated naphthobisthiadiazole (FNTz) for use as a new electron-accepting unit for nonfullerene acceptors. In this letter we report on the design and synthesis of a new electron-transporting π-conjugated polymer containing FNTz and an investigation of the influence of the FNTz unit on the properties and photovoltaic characteristics of the molecule. The introduction of the FNTz unit led to red-shifted absorption and low-lying frontier orbital energy levels, compared to those of NTz. Organic solar cells based on the FNTz–containing polymer, when combined with poly(3-hexylthiophene) as a donor showed an improved power conversion efficiency of 1.13%. These results indicate that FNTz could be an effective electron-accepting unit for electron-transporting polymer.
AbstractList The development of new organic semiconductors for organic solar cell applications continues to be as an important subject. We recently developed fluorinated naphthobisthiadiazole (FNTz) for use as a new electron-accepting unit for nonfullerene acceptors. In this letter we report on the design and synthesis of a new electron-transporting π-conjugated polymer containing FNTz and an investigation of the influence of the FNTz unit on the properties and photovoltaic characteristics of the molecule. The introduction of the FNTz unit led to red-shifted absorption and low-lying frontier orbital energy levels, compared to those of NTz. Organic solar cells based on the FNTz–containing polymer, when combined with poly(3-hexylthiophene) as a donor showed an improved power conversion efficiency of 1.13%. These results indicate that FNTz could be an effective electron-accepting unit for electron-transporting polymer.
Author Moriyama, Taichi
Izuno, Kakeru
Aso, Yoshio
Ie, Yutaka
Author_xml – sequence: 1
  fullname: Ie, Yutaka
  organization: The Institute of Scientific and Industrial Research, Osaka University
– sequence: 2
  fullname: Izuno, Kakeru
  organization: The Institute of Scientific and Industrial Research, Osaka University
– sequence: 3
  fullname: Moriyama, Taichi
  organization: Ishihara Sangyo Kaisha Ltd
– sequence: 4
  fullname: Aso, Yoshio
  organization: The Institute of Scientific and Industrial Research, Osaka University
BookMark eNqFkEFOwzAQRS1UJErhBGxyAZckdtJ6iUoLSBWwKOto4owbV6kd2Q5SWXFDrkSqVhWCBauRRu_N1_xLMjDWICE3STxOueC3bW2DbW2z26Ibs3Q8SZMzMkwYFzRnLB-QYSwSTkXK-QW59H4Tx4xlmRgSf4_v2Nh2iyZEVkVgonmDMjhr6MqB8a11QZt19PVJZ9ZsujUErKLXQ1bUrwJoswcWTWedNkh9V_qgQ7fnnqGtQ21L7UOtodLwYRu8IucKGo_Xxzkib4v5avZIly8PT7O7JZU8ZYGychpnopykZYLTTOK0_0owEDHLUEqe8CplkPMqUZOJQKGUyque5WWWAa9UzEaEHe5KZ713qIrW6S24XZHExb634mdvBUuLPqG3xC9L6gBB95860M0_7uLgbnyANZ7yoO9QNvjHyY7iCZA1uAIN-wa3oJp4
CitedBy_id crossref_primary_10_1002_advs_202405656
crossref_primary_10_1021_acssuschemeng_2c06426
crossref_primary_10_1039_D1TA03219D
Cites_doi 10.1002/aenm.201500195
10.1002/adfm.201504153
10.1002/aenm.201400929
10.1021/ja210687r
10.1021/acsomega.8b00937
10.1038/s41427-018-0088-4
10.1038/nphoton.2015.84
10.1021/acs.orglett.5b02306
10.1038/ncomms6293
10.1021/ar2002446
10.1021/cr900182s
10.2494/photopolymer.30.557
10.1002/adma.201500577
10.1039/C4CS00250D
10.1002/adma.201305999
10.1246/bcsj.64.68
10.1021/cm402421p
10.1021/acs.accounts.5b00363
10.1021/jacs.7b02677
ContentType Journal Article
Copyright 2019 The Society of Photopolymer Science and Technology (SPST)
Copyright_xml – notice: 2019 The Society of Photopolymer Science and Technology (SPST)
DBID AAYXX
CITATION
DOI 10.2494/photopolymer.32.721
DatabaseName CrossRef
DatabaseTitle CrossRef
DatabaseTitleList
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1349-6336
EndPage 725
ExternalDocumentID 10_2494_photopolymer_32_721
article_photopolymer_32_5_32_721_article_char_en
GroupedDBID 2WC
5GY
ACIWK
AENEX
ALMA_UNASSIGNED_HOLDINGS
CS3
DU5
HH5
JSF
JSH
KQ8
OK1
RJT
RNS
RZJ
ZE2
AAYXX
CITATION
ID FETCH-LOGICAL-c423t-3b8059b72b1e85ce872193a9035ecc414d23a64d1f779e9fff6d2b14b55a4df03
ISSN 0914-9244
IngestDate Tue Jul 01 00:20:59 EDT 2025
Thu Apr 24 23:00:20 EDT 2025
Wed Apr 05 06:08:37 EDT 2023
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed false
IsScholarly true
Issue 5
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c423t-3b8059b72b1e85ce872193a9035ecc414d23a64d1f779e9fff6d2b14b55a4df03
OpenAccessLink https://www.jstage.jst.go.jp/article/photopolymer/32/5/32_721/_article/-char/en
PageCount 5
ParticipantIDs crossref_primary_10_2494_photopolymer_32_721
crossref_citationtrail_10_2494_photopolymer_32_721
jstage_primary_article_photopolymer_32_5_32_721_article_char_en
ProviderPackageCode CITATION
AAYXX
PublicationCentury 2000
PublicationDate 2019/06/24
PublicationDateYYYYMMDD 2019-06-24
PublicationDate_xml – month: 06
  year: 2019
  text: 2019/06/24
  day: 24
PublicationDecade 2010
PublicationTitle Journal of Photopolymer Science and Technology
PublicationTitleAlternate J. Photopol. Sci. Technol.
PublicationYear 2019
Publisher The Society of Photopolymer Science and Technology(SPST)
Publisher_xml – name: The Society of Photopolymer Science and Technology(SPST)
References 20. S. Chatterjee, Y. Ie, T. Seo, T. Moriyama, G.-J. A. H. Wetzelaer, P. W. M. Blom, and Y. Aso, NPG Asia Mater., 10 (2018) 1016.
13. I. Osaka, M. Shimawaki, H. Mori, I. Doi, E. Miyazaki, T. Koganezawa, and K. Takimiya, J. Am. Chem. Soc., 134 (2012) 3498.
6. S. Holliday, J. E. Donaghey, and I. McCulloch, Chem. Mater., 26 (2014) 647.
10. W. Zhao, S. Li, H. Yao, S. Zhang, Y. Zhang, B. Yang, and J. Hou, J. Am. Chem. Soc., 139 (2017) 7148.
15. V. Vohra1, K. Kawashima, T. Kakara, T. Koganezawa, I. Osaka, K. Takimiya, and H. Murata, Nat. Photonics, 9 (2015) 403.
9. Y. Liu, L. Zhang, H. Lee, H.-W. Wang, A. Santala, F. Liu, Y. Diao, A. L. Briseno, and T. P. Russell, Adv. Energy Mater., 5 (2015) 1500195.
5. Y. Lin and X. Zhan, Acc. Chem. Res., 49 (2016) 175.
3. J.-S. Wu, S.-W. Cheng, Y.-J. Cheng, and C.-S. Hsu, Chem. Soc. Rev., 44 (2015) 1113.
11. S. Mataka, K. Takahashi, Y. Ikezaki, T. Hatta, A. Tori-i, and M. Tashiro, Bull. Chem. Soc. Jpn., 64 (1991) 68.
19. S. Chatterjee, Y. Ie, and Y. Aso, ACS Omega, 3 (2018) 5814.
12. M. Wang, X. Hu, P. Liu, W. Li, X. Gong, F. Huang, and Y. Cao, J. Am. Chem. Soc., 133 (2011) 9638.
2. Y. Li, Acc. Chem. Res., 45 (2012) 723.
8. O. K. Kwon, J.-H. Park, S. K. Park, and S. Y. Park, Adv. Energy Mater., 5 (2015) 1400929.
18. S. Chatterjee, Y. Ie, and Y. Aso, J. Photopolym. Sci. Technol., 30 (2017) 557.
17. S. Chatterjee, Y. Ie, M. Karakawa, and Y. Aso, Adv. Funct. Mater., 26 (2016) 1161.
4. J. Roncali, P. Leriche, and P. Blanchard, Adv. Mater., 26 (2014) 3821.
16. Y. Ie, S. Sasada, M. Karakawa, and Y. Aso, Org. Lett., 17 (2015) 4580.
7. H. Li, Y.-J. Hwang, B. A. E. Courtright, F. N. Eberle, S. Subramaniyan, and S. A. Jenekhe, Adv. Mater., 27 (2015) 3266.
1. Y.-J. Cheng, S.-H. Yang, and C.-S. Hsu, Chem. Rev., 109 (2009) 5868.
14. Y. Liu, J. Zhao, Z. Li, C. Mu, W. Ma, H. Hu, K. Jiang, H. Lin, H. Ade, and H. Yan, Nat. Commun., 5 (2014) 5293.
11
12
13
14
15
16
17
18
19
1
2
3
4
5
6
7
8
9
20
10
References_xml – reference: 12. M. Wang, X. Hu, P. Liu, W. Li, X. Gong, F. Huang, and Y. Cao, J. Am. Chem. Soc., 133 (2011) 9638.
– reference: 15. V. Vohra1, K. Kawashima, T. Kakara, T. Koganezawa, I. Osaka, K. Takimiya, and H. Murata, Nat. Photonics, 9 (2015) 403.
– reference: 3. J.-S. Wu, S.-W. Cheng, Y.-J. Cheng, and C.-S. Hsu, Chem. Soc. Rev., 44 (2015) 1113.
– reference: 6. S. Holliday, J. E. Donaghey, and I. McCulloch, Chem. Mater., 26 (2014) 647.
– reference: 7. H. Li, Y.-J. Hwang, B. A. E. Courtright, F. N. Eberle, S. Subramaniyan, and S. A. Jenekhe, Adv. Mater., 27 (2015) 3266.
– reference: 14. Y. Liu, J. Zhao, Z. Li, C. Mu, W. Ma, H. Hu, K. Jiang, H. Lin, H. Ade, and H. Yan, Nat. Commun., 5 (2014) 5293.
– reference: 8. O. K. Kwon, J.-H. Park, S. K. Park, and S. Y. Park, Adv. Energy Mater., 5 (2015) 1400929.
– reference: 19. S. Chatterjee, Y. Ie, and Y. Aso, ACS Omega, 3 (2018) 5814.
– reference: 20. S. Chatterjee, Y. Ie, T. Seo, T. Moriyama, G.-J. A. H. Wetzelaer, P. W. M. Blom, and Y. Aso, NPG Asia Mater., 10 (2018) 1016.
– reference: 1. Y.-J. Cheng, S.-H. Yang, and C.-S. Hsu, Chem. Rev., 109 (2009) 5868.
– reference: 18. S. Chatterjee, Y. Ie, and Y. Aso, J. Photopolym. Sci. Technol., 30 (2017) 557.
– reference: 5. Y. Lin and X. Zhan, Acc. Chem. Res., 49 (2016) 175.
– reference: 10. W. Zhao, S. Li, H. Yao, S. Zhang, Y. Zhang, B. Yang, and J. Hou, J. Am. Chem. Soc., 139 (2017) 7148.
– reference: 16. Y. Ie, S. Sasada, M. Karakawa, and Y. Aso, Org. Lett., 17 (2015) 4580.
– reference: 2. Y. Li, Acc. Chem. Res., 45 (2012) 723.
– reference: 9. Y. Liu, L. Zhang, H. Lee, H.-W. Wang, A. Santala, F. Liu, Y. Diao, A. L. Briseno, and T. P. Russell, Adv. Energy Mater., 5 (2015) 1500195.
– reference: 4. J. Roncali, P. Leriche, and P. Blanchard, Adv. Mater., 26 (2014) 3821.
– reference: 17. S. Chatterjee, Y. Ie, M. Karakawa, and Y. Aso, Adv. Funct. Mater., 26 (2016) 1161.
– reference: 13. I. Osaka, M. Shimawaki, H. Mori, I. Doi, E. Miyazaki, T. Koganezawa, and K. Takimiya, J. Am. Chem. Soc., 134 (2012) 3498.
– reference: 11. S. Mataka, K. Takahashi, Y. Ikezaki, T. Hatta, A. Tori-i, and M. Tashiro, Bull. Chem. Soc. Jpn., 64 (1991) 68.
– ident: 9
  doi: 10.1002/aenm.201500195
– ident: 17
  doi: 10.1002/adfm.201504153
– ident: 8
  doi: 10.1002/aenm.201400929
– ident: 13
  doi: 10.1021/ja210687r
– ident: 19
  doi: 10.1021/acsomega.8b00937
– ident: 20
  doi: 10.1038/s41427-018-0088-4
– ident: 12
– ident: 15
  doi: 10.1038/nphoton.2015.84
– ident: 16
  doi: 10.1021/acs.orglett.5b02306
– ident: 14
  doi: 10.1038/ncomms6293
– ident: 2
  doi: 10.1021/ar2002446
– ident: 1
  doi: 10.1021/cr900182s
– ident: 18
  doi: 10.2494/photopolymer.30.557
– ident: 7
  doi: 10.1002/adma.201500577
– ident: 3
  doi: 10.1039/C4CS00250D
– ident: 4
  doi: 10.1002/adma.201305999
– ident: 11
  doi: 10.1246/bcsj.64.68
– ident: 6
  doi: 10.1021/cm402421p
– ident: 5
  doi: 10.1021/acs.accounts.5b00363
– ident: 10
  doi: 10.1021/jacs.7b02677
SSID ssj0033559
Score 2.1837337
Snippet The development of new organic semiconductors for organic solar cell applications continues to be as an important subject. We recently developed fluorinated...
SourceID crossref
jstage
SourceType Enrichment Source
Index Database
Publisher
StartPage 721
SubjectTerms Acceptor
Fluorinated naphthobisthiadiazole
Organic semiconductors
Organic solar cell
Structure-property relationship
Title Development of an Electron-Transporting π-Conjugated Polymer Containing Fluorine-substituted Naphthobisthiadiazole
URI https://www.jstage.jst.go.jp/article/photopolymer/32/5/32_721/_article/-char/en
Volume 32
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
ispartofPNX Journal of Photopolymer Science and Technology, 2019/06/24, Vol.32(5), pp.721-725
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9QwEDZtQaIXxKui5SEf4LR4SWLndUJo1VVLBSrqVmpPkZ042m23SbWbHLon_iF_ibGd19IItXCJVtHYO8l8GY_H80Dofezaqc0tQSjoOsKE5ITDOkNSoc5y0zBgQvkhv333Dk7Z1zP3bGPzQSdqqSzEMF715pX8i1ThHshVZcneQ7LNpHADfoN84QoShuudZNyJ-NHn-dlgv-pqQ5qi5doVMBp_CCwyyrOLUrnNEhX2dnMlFyrhrzA9IgbjeamC8SRZgi4xAQQJKN9r5TgVAIbpTJUxWOXz9eCh1qA9nuaFarmgJ651hvLL33bfH2o36nlZ8MtmWThclboN-OCIX8pF2SABmLrhV9rGnfBZPJ01GF1q8vN8OTXBZLX3QiVMecRpvZfqW6jDU-_GKNjdJ8cnk9pPUvkybUZgI2nmlUaTUxYSj5rqKrWqb12p7WG61tu-SdOuTADf5GL_ubrATpWplsgdJofUGTZj18p2V6CIutQRdSJXXWBIVBOo7DoA8yZ66MBOR6nqox_NQRgFc9CUi6ye0BTOUpx86uFjzbh6dAH7izo2UZtLk6foSQUL_MX8_TO0IbPn6PGobi_4Ai074MV5inmGe8GLf_3sABdXwMUtcHEfcHEvcF-i0_H-ZHRAqg4gJAYzvyBUBGD-C98RtgzcWAbwjCHloUVdUD3MZolDuccSO_X9UIZpmnoJ0DLhupwlqUV30FaWZ_IVwl7qW17CmEd9QIaMuQiAwA3CRIQes-1d5NSvLoqr8viqS8s8gm2yet-3JAm87KKPzaBrUx3m7-SfjUwa4vuiZO-_Z3iNttvv8A3aKhalfAt2dSHeaeT9BpI74-M
linkProvider Colorado Alliance of Research Libraries
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Development+of+an+Electron-Transporting+%CF%80-Conjugated+Polymer+Containing+Fluorine-substituted+Naphthobisthiadiazole&rft.jtitle=Journal+of+Photopolymer+Science+and+Technology&rft.au=Ie%2C+Yutaka&rft.au=Izuno%2C+Kakeru&rft.au=Moriyama%2C+Taichi&rft.au=Aso%2C+Yoshio&rft.date=2019-06-24&rft.pub=The+Society+of+Photopolymer+Science+and+Technology%28SPST%29&rft.issn=0914-9244&rft.eissn=1349-6336&rft.volume=32&rft.issue=5&rft.spage=721&rft.epage=725&rft_id=info:doi/10.2494%2Fphotopolymer.32.721&rft.externalDocID=article_photopolymer_32_5_32_721_article_char_en
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0914-9244&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0914-9244&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0914-9244&client=summon