Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors

We designed and synthesized a series of fused-ring electron acceptors (FREAs) based on naphthalene-fused octacyclic cores end-capped by 3-(1,1-dicyanomethylene)-5,6-difluoro-1- indanone (NOICs) using a bottom-up approach. The NOIC series shares the same end groups and side chains, as well as similar...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2020-11, Vol.142 (47), p.20124-20133
Hauptverfasser: Li, Tengfei, Wu, Yao, Zhou, Jiadong, Li, Mengyang, Wu, Jingnan, Hu, Qin, Jia, Boyu, Pan, Xiran, Zhang, Maojie, Tang, Zheng, Xie, Zengqi, Russell, Thomas P, Zhan, Xiaowei
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 20133
container_issue 47
container_start_page 20124
container_title Journal of the American Chemical Society
container_volume 142
creator Li, Tengfei
Wu, Yao
Zhou, Jiadong
Li, Mengyang
Wu, Jingnan
Hu, Qin
Jia, Boyu
Pan, Xiran
Zhang, Maojie
Tang, Zheng
Xie, Zengqi
Russell, Thomas P
Zhan, Xiaowei
description We designed and synthesized a series of fused-ring electron acceptors (FREAs) based on naphthalene-fused octacyclic cores end-capped by 3-(1,1-dicyanomethylene)-5,6-difluoro-1- indanone (NOICs) using a bottom-up approach. The NOIC series shares the same end groups and side chains, as well as similar fused-ring cores. The butterfly effects, arising from different methoxy positions in the starting materials, impact the design of the final FREAs, as well as their molecular packing, optical and electronic properties, charge transport, film morphology, and performance of organic solar cells. The binary-blend devices based on this NOIC series show power conversion efficiencies varying from 7.15% to 14.1%, due to the different intrinsic properties of the NOIC series, morphologies of blend films, and voltage losses of devices.
doi_str_mv 10.1021/jacs.0c09800
format Article
fullrecord <record><control><sourceid>proquest_osti_</sourceid><recordid>TN_cdi_osti_scitechconnect_1839250</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2459624539</sourcerecordid><originalsourceid>FETCH-LOGICAL-a432t-959cee11c5a560d704054e1ad642de76ca75c38cf5c69b7fa26b4df9d5492c853</originalsourceid><addsrcrecordid>eNptkE9LAzEQxYMoWKs3P8DiyYNbk2yS3RxrqX-gIlQ9h3Q20ZTtpibZg9_eLBW8eJnhPX4zzDyELgmeEUzJ7VZDnGHAssH4CE0Ip7jkhIpjNMEY07JuRHWKzmLcZsloQyZofTekZILtvoultQZSLObBRdd_FDb4XfGadEijetYZc7qLheuL-yGatlyP_rLLQ8H3xRzA7JMP8Ryd2MyZi98-Re_3y7fFY7l6eXhazFelZhVNpeQSjCEEuOYCtzVmmDNDdCsYbU0tQNccqgYsByE3tdVUbFhrZcuZpNDwaoquDnt9TE5FcMnAJ_i-zwcp0lSScpyh6wO0D_5rMDGpnYtguk73xg9RUcalyKWSGb05oBB8jMFYtQ9up8O3IliN-aoxX_Wb79_m0dz6IfT52f_RH2Aqewc</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2459624539</pqid></control><display><type>article</type><title>Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors</title><source>American Chemical Society Journals</source><creator>Li, Tengfei ; Wu, Yao ; Zhou, Jiadong ; Li, Mengyang ; Wu, Jingnan ; Hu, Qin ; Jia, Boyu ; Pan, Xiran ; Zhang, Maojie ; Tang, Zheng ; Xie, Zengqi ; Russell, Thomas P ; Zhan, Xiaowei</creator><creatorcontrib>Li, Tengfei ; Wu, Yao ; Zhou, Jiadong ; Li, Mengyang ; Wu, Jingnan ; Hu, Qin ; Jia, Boyu ; Pan, Xiran ; Zhang, Maojie ; Tang, Zheng ; Xie, Zengqi ; Russell, Thomas P ; Zhan, Xiaowei ; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)</creatorcontrib><description>We designed and synthesized a series of fused-ring electron acceptors (FREAs) based on naphthalene-fused octacyclic cores end-capped by 3-(1,1-dicyanomethylene)-5,6-difluoro-1- indanone (NOICs) using a bottom-up approach. The NOIC series shares the same end groups and side chains, as well as similar fused-ring cores. The butterfly effects, arising from different methoxy positions in the starting materials, impact the design of the final FREAs, as well as their molecular packing, optical and electronic properties, charge transport, film morphology, and performance of organic solar cells. The binary-blend devices based on this NOIC series show power conversion efficiencies varying from 7.15% to 14.1%, due to the different intrinsic properties of the NOIC series, morphologies of blend films, and voltage losses of devices.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.0c09800</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Absorption ; External quantum efficiency ; INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY ; Materials ; Molecular structure ; Photovoltaics</subject><ispartof>Journal of the American Chemical Society, 2020-11, Vol.142 (47), p.20124-20133</ispartof><rights>2020 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a432t-959cee11c5a560d704054e1ad642de76ca75c38cf5c69b7fa26b4df9d5492c853</citedby><cites>FETCH-LOGICAL-a432t-959cee11c5a560d704054e1ad642de76ca75c38cf5c69b7fa26b4df9d5492c853</cites><orcidid>0000-0001-6384-5826 ; 0000-0003-0826-840X ; 0000-0002-6680-7347 ; 0000-0002-0501-1505 ; 0000-0002-1006-3342 ; 0000-0002-6102-5856 ; 0000-0003-0036-2362 ; 0000000261025856 ; 0000000266807347 ; 0000000300362362 ; 0000000210063342 ; 000000030826840X ; 0000000163845826 ; 0000000205011505</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jacs.0c09800$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.0c09800$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.osti.gov/servlets/purl/1839250$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Tengfei</creatorcontrib><creatorcontrib>Wu, Yao</creatorcontrib><creatorcontrib>Zhou, Jiadong</creatorcontrib><creatorcontrib>Li, Mengyang</creatorcontrib><creatorcontrib>Wu, Jingnan</creatorcontrib><creatorcontrib>Hu, Qin</creatorcontrib><creatorcontrib>Jia, Boyu</creatorcontrib><creatorcontrib>Pan, Xiran</creatorcontrib><creatorcontrib>Zhang, Maojie</creatorcontrib><creatorcontrib>Tang, Zheng</creatorcontrib><creatorcontrib>Xie, Zengqi</creatorcontrib><creatorcontrib>Russell, Thomas P</creatorcontrib><creatorcontrib>Zhan, Xiaowei</creatorcontrib><creatorcontrib>Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)</creatorcontrib><title>Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>We designed and synthesized a series of fused-ring electron acceptors (FREAs) based on naphthalene-fused octacyclic cores end-capped by 3-(1,1-dicyanomethylene)-5,6-difluoro-1- indanone (NOICs) using a bottom-up approach. The NOIC series shares the same end groups and side chains, as well as similar fused-ring cores. The butterfly effects, arising from different methoxy positions in the starting materials, impact the design of the final FREAs, as well as their molecular packing, optical and electronic properties, charge transport, film morphology, and performance of organic solar cells. The binary-blend devices based on this NOIC series show power conversion efficiencies varying from 7.15% to 14.1%, due to the different intrinsic properties of the NOIC series, morphologies of blend films, and voltage losses of devices.</description><subject>Absorption</subject><subject>External quantum efficiency</subject><subject>INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</subject><subject>Materials</subject><subject>Molecular structure</subject><subject>Photovoltaics</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNptkE9LAzEQxYMoWKs3P8DiyYNbk2yS3RxrqX-gIlQ9h3Q20ZTtpibZg9_eLBW8eJnhPX4zzDyELgmeEUzJ7VZDnGHAssH4CE0Ip7jkhIpjNMEY07JuRHWKzmLcZsloQyZofTekZILtvoultQZSLObBRdd_FDb4XfGadEijetYZc7qLheuL-yGatlyP_rLLQ8H3xRzA7JMP8Ryd2MyZi98-Re_3y7fFY7l6eXhazFelZhVNpeQSjCEEuOYCtzVmmDNDdCsYbU0tQNccqgYsByE3tdVUbFhrZcuZpNDwaoquDnt9TE5FcMnAJ_i-zwcp0lSScpyh6wO0D_5rMDGpnYtguk73xg9RUcalyKWSGb05oBB8jMFYtQ9up8O3IliN-aoxX_Wb79_m0dz6IfT52f_RH2Aqewc</recordid><startdate>20201125</startdate><enddate>20201125</enddate><creator>Li, Tengfei</creator><creator>Wu, Yao</creator><creator>Zhou, Jiadong</creator><creator>Li, Mengyang</creator><creator>Wu, Jingnan</creator><creator>Hu, Qin</creator><creator>Jia, Boyu</creator><creator>Pan, Xiran</creator><creator>Zhang, Maojie</creator><creator>Tang, Zheng</creator><creator>Xie, Zengqi</creator><creator>Russell, Thomas P</creator><creator>Zhan, Xiaowei</creator><general>American Chemical Society</general><general>American Chemical Society (ACS)</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>OIOZB</scope><scope>OTOTI</scope><orcidid>https://orcid.org/0000-0001-6384-5826</orcidid><orcidid>https://orcid.org/0000-0003-0826-840X</orcidid><orcidid>https://orcid.org/0000-0002-6680-7347</orcidid><orcidid>https://orcid.org/0000-0002-0501-1505</orcidid><orcidid>https://orcid.org/0000-0002-1006-3342</orcidid><orcidid>https://orcid.org/0000-0002-6102-5856</orcidid><orcidid>https://orcid.org/0000-0003-0036-2362</orcidid><orcidid>https://orcid.org/0000000261025856</orcidid><orcidid>https://orcid.org/0000000266807347</orcidid><orcidid>https://orcid.org/0000000300362362</orcidid><orcidid>https://orcid.org/0000000210063342</orcidid><orcidid>https://orcid.org/000000030826840X</orcidid><orcidid>https://orcid.org/0000000163845826</orcidid><orcidid>https://orcid.org/0000000205011505</orcidid></search><sort><creationdate>20201125</creationdate><title>Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors</title><author>Li, Tengfei ; Wu, Yao ; Zhou, Jiadong ; Li, Mengyang ; Wu, Jingnan ; Hu, Qin ; Jia, Boyu ; Pan, Xiran ; Zhang, Maojie ; Tang, Zheng ; Xie, Zengqi ; Russell, Thomas P ; Zhan, Xiaowei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a432t-959cee11c5a560d704054e1ad642de76ca75c38cf5c69b7fa26b4df9d5492c853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Absorption</topic><topic>External quantum efficiency</topic><topic>INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</topic><topic>Materials</topic><topic>Molecular structure</topic><topic>Photovoltaics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Tengfei</creatorcontrib><creatorcontrib>Wu, Yao</creatorcontrib><creatorcontrib>Zhou, Jiadong</creatorcontrib><creatorcontrib>Li, Mengyang</creatorcontrib><creatorcontrib>Wu, Jingnan</creatorcontrib><creatorcontrib>Hu, Qin</creatorcontrib><creatorcontrib>Jia, Boyu</creatorcontrib><creatorcontrib>Pan, Xiran</creatorcontrib><creatorcontrib>Zhang, Maojie</creatorcontrib><creatorcontrib>Tang, Zheng</creatorcontrib><creatorcontrib>Xie, Zengqi</creatorcontrib><creatorcontrib>Russell, Thomas P</creatorcontrib><creatorcontrib>Zhan, Xiaowei</creatorcontrib><creatorcontrib>Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>OSTI.GOV - Hybrid</collection><collection>OSTI.GOV</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Tengfei</au><au>Wu, Yao</au><au>Zhou, Jiadong</au><au>Li, Mengyang</au><au>Wu, Jingnan</au><au>Hu, Qin</au><au>Jia, Boyu</au><au>Pan, Xiran</au><au>Zhang, Maojie</au><au>Tang, Zheng</au><au>Xie, Zengqi</au><au>Russell, Thomas P</au><au>Zhan, Xiaowei</au><aucorp>Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2020-11-25</date><risdate>2020</risdate><volume>142</volume><issue>47</issue><spage>20124</spage><epage>20133</epage><pages>20124-20133</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>We designed and synthesized a series of fused-ring electron acceptors (FREAs) based on naphthalene-fused octacyclic cores end-capped by 3-(1,1-dicyanomethylene)-5,6-difluoro-1- indanone (NOICs) using a bottom-up approach. The NOIC series shares the same end groups and side chains, as well as similar fused-ring cores. The butterfly effects, arising from different methoxy positions in the starting materials, impact the design of the final FREAs, as well as their molecular packing, optical and electronic properties, charge transport, film morphology, and performance of organic solar cells. The binary-blend devices based on this NOIC series show power conversion efficiencies varying from 7.15% to 14.1%, due to the different intrinsic properties of the NOIC series, morphologies of blend films, and voltage losses of devices.</abstract><cop>United States</cop><pub>American Chemical Society</pub><doi>10.1021/jacs.0c09800</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-6384-5826</orcidid><orcidid>https://orcid.org/0000-0003-0826-840X</orcidid><orcidid>https://orcid.org/0000-0002-6680-7347</orcidid><orcidid>https://orcid.org/0000-0002-0501-1505</orcidid><orcidid>https://orcid.org/0000-0002-1006-3342</orcidid><orcidid>https://orcid.org/0000-0002-6102-5856</orcidid><orcidid>https://orcid.org/0000-0003-0036-2362</orcidid><orcidid>https://orcid.org/0000000261025856</orcidid><orcidid>https://orcid.org/0000000266807347</orcidid><orcidid>https://orcid.org/0000000300362362</orcidid><orcidid>https://orcid.org/0000000210063342</orcidid><orcidid>https://orcid.org/000000030826840X</orcidid><orcidid>https://orcid.org/0000000163845826</orcidid><orcidid>https://orcid.org/0000000205011505</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2020-11, Vol.142 (47), p.20124-20133
issn 0002-7863
1520-5126
language eng
recordid cdi_osti_scitechconnect_1839250
source American Chemical Society Journals
subjects Absorption
External quantum efficiency
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Materials
Molecular structure
Photovoltaics
title Butterfly Effects Arising from Starting Materials in Fused-Ring Electron Acceptors
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T06%3A50%3A14IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_osti_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Butterfly%20Effects%20Arising%20from%20Starting%20Materials%20in%20Fused-Ring%20Electron%20Acceptors&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Li,%20Tengfei&rft.aucorp=Lawrence%20Berkeley%20National%20Lab.%20(LBNL),%20Berkeley,%20CA%20(United%20States)&rft.date=2020-11-25&rft.volume=142&rft.issue=47&rft.spage=20124&rft.epage=20133&rft.pages=20124-20133&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.0c09800&rft_dat=%3Cproquest_osti_%3E2459624539%3C/proquest_osti_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2459624539&rft_id=info:pmid/&rfr_iscdi=true