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...
Gespeichert in:
Veröffentlicht in: | Journal of the American Chemical Society 2020-11, Vol.142 (47), p.20124-20133 |
---|---|
Hauptverfasser: | , , , , , , , , , , , , |
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 |