Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells
Two BODIPY derivatives with one ( B2 ) and two ( B3 ) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). Their optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in orga...
Gespeichert in:
Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2020-05, Vol.49 (17), p.566-5617 |
---|---|
Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 5617 |
---|---|
container_issue | 17 |
container_start_page | 566 |
container_title | Dalton transactions : an international journal of inorganic chemistry |
container_volume | 49 |
creator | Yang, Jian Devillers, Charles H Fleurat-Lessard, Paul Jiang, Hao Wang, Shifa Gros, Claude P Gupta, Gaurav Sharma, Ganesh D Xu, Haijun |
description | Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). Their optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in organic solvents and present high molar extinction coefficients (1.37-1.48 × 10
5
M
−1
cm
−1
) in solutions with absorption maxima at 586 nm for mono-styryl groups and at 672 nm for di-styryl groups. The introduction of the styryl moieties results in a large bathochromic shift and a significant decrease in the HOMO-LUMO energy-gaps. The BODIPY dyes show relatively low HOMO energies ranging from −4.99 to −5.16 eV as determined from cyclic voltammetry measurements. Cyclic voltammetry measurements and theoretical calculations demonstrate that the frontier molecular orbital levels of these compounds match with those of PC
71
BM as the acceptor, supporting their application as donor materials in solution-processed small molecule bulk heterojunction (BHJ) organic solar cells. After the optimization of the active layer,
B2
:PC
71
BM and
B3
:PC
71
BM based organic solar cells showed an overall power conversion efficiency of 6.41% and 7.47%, respectively. The higher PCE of the
B3
-based OSC is ascribed to the more balanced charge transport and exciton dissociation, better crystallinity and molecular packing.
Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV), showing an overall PCE of 6.41% and 7.47%, respectively. |
doi_str_mv | 10.1039/d0dt00637h |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D0DT00637H</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2398138993</sourcerecordid><originalsourceid>FETCH-LOGICAL-c373t-29d2c97708561e0a4959837c52be023bcec3b417e6392240d3ff77229bbd2ed3</originalsourceid><addsrcrecordid>eNpdkbtPwzAQxi0E4lFY2EGWWBBSwLGTOB6hBVqpUhm6MEV-XNqUNAY7Gcpfj_ugSEz36e6nT3f3IXQZk_uYMPFgiGkJyRifH6DTOOE8EpQlh3tNsxN05v2CEEpJSo_RCaM0T0kiTlHdl07Jb1tDpKQHg2cOoMGyMVjVHURPk8Ho7R2blTR-021dtZEeG9tY53FpHVZd_YHn0IKzi67RbWUbbN1MNpXG3tbSYQ117c_RUSlrDxe72kPTl-dpfxiNJ6-j_uM40oyzNqLCUC04J3maxUBkIlKRM65TqoBQpjRoppKYQ8bCcQkxrCw5p1QoZSgY1kO3W9tPZ7868G2xrPx6AdmA7XxBWS4ywbLg1UM3_9CF7VwTlguUyONAChaouy2lnfXeQVl8umop3aqISbGOoBiQwXQTwTDA1zvLTi3B7NHfnwfgags4r_fTvwzZD8kQiiE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2398138993</pqid></control><display><type>article</type><title>Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Yang, Jian ; Devillers, Charles H ; Fleurat-Lessard, Paul ; Jiang, Hao ; Wang, Shifa ; Gros, Claude P ; Gupta, Gaurav ; Sharma, Ganesh D ; Xu, Haijun</creator><creatorcontrib>Yang, Jian ; Devillers, Charles H ; Fleurat-Lessard, Paul ; Jiang, Hao ; Wang, Shifa ; Gros, Claude P ; Gupta, Gaurav ; Sharma, Ganesh D ; Xu, Haijun</creatorcontrib><description>Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). Their optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in organic solvents and present high molar extinction coefficients (1.37-1.48 × 10
5
M
−1
cm
−1
) in solutions with absorption maxima at 586 nm for mono-styryl groups and at 672 nm for di-styryl groups. The introduction of the styryl moieties results in a large bathochromic shift and a significant decrease in the HOMO-LUMO energy-gaps. The BODIPY dyes show relatively low HOMO energies ranging from −4.99 to −5.16 eV as determined from cyclic voltammetry measurements. Cyclic voltammetry measurements and theoretical calculations demonstrate that the frontier molecular orbital levels of these compounds match with those of PC
71
BM as the acceptor, supporting their application as donor materials in solution-processed small molecule bulk heterojunction (BHJ) organic solar cells. After the optimization of the active layer,
B2
:PC
71
BM and
B3
:PC
71
BM based organic solar cells showed an overall power conversion efficiency of 6.41% and 7.47%, respectively. The higher PCE of the
B3
-based OSC is ascribed to the more balanced charge transport and exciton dissociation, better crystallinity and molecular packing.
Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV), showing an overall PCE of 6.41% and 7.47%, respectively.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d0dt00637h</identifier><identifier>PMID: 32285049</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Carbazoles ; Charge transport ; Donor materials ; Donors (electronic) ; Dyes ; Electrochemical analysis ; Energy conversion efficiency ; Energy gap ; Excitons ; Heterojunctions ; Mathematical analysis ; Molecular orbitals ; Optical properties ; Optimization ; Photovoltaic cells ; Solar cells ; Voltammetry</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2020-05, Vol.49 (17), p.566-5617</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c373t-29d2c97708561e0a4959837c52be023bcec3b417e6392240d3ff77229bbd2ed3</citedby><cites>FETCH-LOGICAL-c373t-29d2c97708561e0a4959837c52be023bcec3b417e6392240d3ff77229bbd2ed3</cites><orcidid>0000-0002-1717-0116 ; 0000-0002-8721-3310 ; 0000-0001-9078-7035 ; 0000-0001-8578-9845 ; 0000-0002-6966-947X ; 0000-0003-3114-2522 ; 0000-0003-2272-474X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32285049$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Jian</creatorcontrib><creatorcontrib>Devillers, Charles H</creatorcontrib><creatorcontrib>Fleurat-Lessard, Paul</creatorcontrib><creatorcontrib>Jiang, Hao</creatorcontrib><creatorcontrib>Wang, Shifa</creatorcontrib><creatorcontrib>Gros, Claude P</creatorcontrib><creatorcontrib>Gupta, Gaurav</creatorcontrib><creatorcontrib>Sharma, Ganesh D</creatorcontrib><creatorcontrib>Xu, Haijun</creatorcontrib><title>Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). Their optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in organic solvents and present high molar extinction coefficients (1.37-1.48 × 10
5
M
−1
cm
−1
) in solutions with absorption maxima at 586 nm for mono-styryl groups and at 672 nm for di-styryl groups. The introduction of the styryl moieties results in a large bathochromic shift and a significant decrease in the HOMO-LUMO energy-gaps. The BODIPY dyes show relatively low HOMO energies ranging from −4.99 to −5.16 eV as determined from cyclic voltammetry measurements. Cyclic voltammetry measurements and theoretical calculations demonstrate that the frontier molecular orbital levels of these compounds match with those of PC
71
BM as the acceptor, supporting their application as donor materials in solution-processed small molecule bulk heterojunction (BHJ) organic solar cells. After the optimization of the active layer,
B2
:PC
71
BM and
B3
:PC
71
BM based organic solar cells showed an overall power conversion efficiency of 6.41% and 7.47%, respectively. The higher PCE of the
B3
-based OSC is ascribed to the more balanced charge transport and exciton dissociation, better crystallinity and molecular packing.
Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV), showing an overall PCE of 6.41% and 7.47%, respectively.</description><subject>Carbazoles</subject><subject>Charge transport</subject><subject>Donor materials</subject><subject>Donors (electronic)</subject><subject>Dyes</subject><subject>Electrochemical analysis</subject><subject>Energy conversion efficiency</subject><subject>Energy gap</subject><subject>Excitons</subject><subject>Heterojunctions</subject><subject>Mathematical analysis</subject><subject>Molecular orbitals</subject><subject>Optical properties</subject><subject>Optimization</subject><subject>Photovoltaic cells</subject><subject>Solar cells</subject><subject>Voltammetry</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpdkbtPwzAQxi0E4lFY2EGWWBBSwLGTOB6hBVqpUhm6MEV-XNqUNAY7Gcpfj_ugSEz36e6nT3f3IXQZk_uYMPFgiGkJyRifH6DTOOE8EpQlh3tNsxN05v2CEEpJSo_RCaM0T0kiTlHdl07Jb1tDpKQHg2cOoMGyMVjVHURPk8Ho7R2blTR-021dtZEeG9tY53FpHVZd_YHn0IKzi67RbWUbbN1MNpXG3tbSYQ117c_RUSlrDxe72kPTl-dpfxiNJ6-j_uM40oyzNqLCUC04J3maxUBkIlKRM65TqoBQpjRoppKYQ8bCcQkxrCw5p1QoZSgY1kO3W9tPZ7868G2xrPx6AdmA7XxBWS4ywbLg1UM3_9CF7VwTlguUyONAChaouy2lnfXeQVl8umop3aqISbGOoBiQwXQTwTDA1zvLTi3B7NHfnwfgags4r_fTvwzZD8kQiiE</recordid><startdate>20200507</startdate><enddate>20200507</enddate><creator>Yang, Jian</creator><creator>Devillers, Charles H</creator><creator>Fleurat-Lessard, Paul</creator><creator>Jiang, Hao</creator><creator>Wang, Shifa</creator><creator>Gros, Claude P</creator><creator>Gupta, Gaurav</creator><creator>Sharma, Ganesh D</creator><creator>Xu, Haijun</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1717-0116</orcidid><orcidid>https://orcid.org/0000-0002-8721-3310</orcidid><orcidid>https://orcid.org/0000-0001-9078-7035</orcidid><orcidid>https://orcid.org/0000-0001-8578-9845</orcidid><orcidid>https://orcid.org/0000-0002-6966-947X</orcidid><orcidid>https://orcid.org/0000-0003-3114-2522</orcidid><orcidid>https://orcid.org/0000-0003-2272-474X</orcidid></search><sort><creationdate>20200507</creationdate><title>Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells</title><author>Yang, Jian ; Devillers, Charles H ; Fleurat-Lessard, Paul ; Jiang, Hao ; Wang, Shifa ; Gros, Claude P ; Gupta, Gaurav ; Sharma, Ganesh D ; Xu, Haijun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-29d2c97708561e0a4959837c52be023bcec3b417e6392240d3ff77229bbd2ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Carbazoles</topic><topic>Charge transport</topic><topic>Donor materials</topic><topic>Donors (electronic)</topic><topic>Dyes</topic><topic>Electrochemical analysis</topic><topic>Energy conversion efficiency</topic><topic>Energy gap</topic><topic>Excitons</topic><topic>Heterojunctions</topic><topic>Mathematical analysis</topic><topic>Molecular orbitals</topic><topic>Optical properties</topic><topic>Optimization</topic><topic>Photovoltaic cells</topic><topic>Solar cells</topic><topic>Voltammetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Jian</creatorcontrib><creatorcontrib>Devillers, Charles H</creatorcontrib><creatorcontrib>Fleurat-Lessard, Paul</creatorcontrib><creatorcontrib>Jiang, Hao</creatorcontrib><creatorcontrib>Wang, Shifa</creatorcontrib><creatorcontrib>Gros, Claude P</creatorcontrib><creatorcontrib>Gupta, Gaurav</creatorcontrib><creatorcontrib>Sharma, Ganesh D</creatorcontrib><creatorcontrib>Xu, Haijun</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Jian</au><au>Devillers, Charles H</au><au>Fleurat-Lessard, Paul</au><au>Jiang, Hao</au><au>Wang, Shifa</au><au>Gros, Claude P</au><au>Gupta, Gaurav</au><au>Sharma, Ganesh D</au><au>Xu, Haijun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2020-05-07</date><risdate>2020</risdate><volume>49</volume><issue>17</issue><spage>566</spage><epage>5617</epage><pages>566-5617</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). Their optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in organic solvents and present high molar extinction coefficients (1.37-1.48 × 10
5
M
−1
cm
−1
) in solutions with absorption maxima at 586 nm for mono-styryl groups and at 672 nm for di-styryl groups. The introduction of the styryl moieties results in a large bathochromic shift and a significant decrease in the HOMO-LUMO energy-gaps. The BODIPY dyes show relatively low HOMO energies ranging from −4.99 to −5.16 eV as determined from cyclic voltammetry measurements. Cyclic voltammetry measurements and theoretical calculations demonstrate that the frontier molecular orbital levels of these compounds match with those of PC
71
BM as the acceptor, supporting their application as donor materials in solution-processed small molecule bulk heterojunction (BHJ) organic solar cells. After the optimization of the active layer,
B2
:PC
71
BM and
B3
:PC
71
BM based organic solar cells showed an overall power conversion efficiency of 6.41% and 7.47%, respectively. The higher PCE of the
B3
-based OSC is ascribed to the more balanced charge transport and exciton dissociation, better crystallinity and molecular packing.
Two BODIPY derivatives with one (
B2
) and two (
B3
) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV), showing an overall PCE of 6.41% and 7.47%, respectively.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32285049</pmid><doi>10.1039/d0dt00637h</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-1717-0116</orcidid><orcidid>https://orcid.org/0000-0002-8721-3310</orcidid><orcidid>https://orcid.org/0000-0001-9078-7035</orcidid><orcidid>https://orcid.org/0000-0001-8578-9845</orcidid><orcidid>https://orcid.org/0000-0002-6966-947X</orcidid><orcidid>https://orcid.org/0000-0003-3114-2522</orcidid><orcidid>https://orcid.org/0000-0003-2272-474X</orcidid><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1477-9226 |
ispartof | Dalton transactions : an international journal of inorganic chemistry, 2020-05, Vol.49 (17), p.566-5617 |
issn | 1477-9226 1477-9234 |
language | eng |
recordid | cdi_crossref_primary_10_1039_D0DT00637H |
source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Carbazoles Charge transport Donor materials Donors (electronic) Dyes Electrochemical analysis Energy conversion efficiency Energy gap Excitons Heterojunctions Mathematical analysis Molecular orbitals Optical properties Optimization Photovoltaic cells Solar cells Voltammetry |
title | Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T06%3A24%3A11IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Carbazole-based%20green%20and%20blue-BODIPY%20dyads%20and%20triads%20as%20donors%20for%20bulk%20heterojunction%20organic%20solar%20cells&rft.jtitle=Dalton%20transactions%20:%20an%20international%20journal%20of%20inorganic%20chemistry&rft.au=Yang,%20Jian&rft.date=2020-05-07&rft.volume=49&rft.issue=17&rft.spage=566&rft.epage=5617&rft.pages=566-5617&rft.issn=1477-9226&rft.eissn=1477-9234&rft_id=info:doi/10.1039/d0dt00637h&rft_dat=%3Cproquest_cross%3E2398138993%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2398138993&rft_id=info:pmid/32285049&rfr_iscdi=true |