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Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts
Developing electrochromic materials with energy-saving ( i.e. , low driving voltage) and long-life ( i.e. , high switching stability) properties is highly desirable with respect to practical application. In this work, we report the synthesis of two N , N ′-di(4-pyridyl)-1,4,5,8-naphthalene diimide d...
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| Published in: | Journal of materials chemistry. C, Materials for optical and electronic devices Materials for optical and electronic devices, 2020-08, Vol.8 (29), p.131-138 |
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| container_end_page | 138 |
| container_issue | 29 |
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| container_title | Journal of materials chemistry. C, Materials for optical and electronic devices |
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| creator | Li, Feng Huang, Zhen-jie Zhou, Qian-hua Pan, Ming-yue Tang, Qian Gong, Cheng-bin |
| description | Developing electrochromic materials with energy-saving (
i.e.
, low driving voltage) and long-life (
i.e.
, high switching stability) properties is highly desirable with respect to practical application. In this work, we report the synthesis of two
N
,
N
′-di(4-pyridyl)-1,4,5,8-naphthalene diimide derivatives (DPNDIs), (Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br), and the characterization of their electrochemical and electrochromic properties. Both DPNDIs showed two quasi-reversible redox couples in the cyclic voltammograms with cathodic peak potentials of approximately −0.30 and −0.70 V
vs.
Ag/Ag
+
. The electrochromic devices based on ((Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br)) gave a colored state of dark orange and orange, respectively, which are colored states that have rarely been reported, and both DPNDIs had a low onset bias of −0.7 V and good switching stabilities (the change in optical contrast after 7200 s of |
| doi_str_mv | 10.1039/d0tc00250j |
| format | article |
| fullrecord | <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_proquest_journals_2428378764</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2428378764</sourcerecordid><originalsourceid>FETCH-LOGICAL-c344t-3ad52e1ec1ce8bd74ca0edf0abac4d6b1454711e0080756be4cb380628db6e5f3</originalsourceid><addsrcrecordid>eNp9kM1LAzEQxYMoWGov3oWIN2F1sslmt0ep9YuCl3pesslsm7KbrMlW6H_f1Uq9OZcZeL-ZNzxCLhncMeDTewO9Bkgz2JyQUQoZJHnGxelxTuU5mcS4gaEKJgs5HZFq7jCsdklUX9atqHKGNt6tksbWSLFB3Qev18G3VtNW9RisaiL1NXWqW_dr1aBDaqxtrcFE-4CGdrtgjXV229Komj5ekLN6WMLJbx-Tj6f5cvaSLN6fX2cPi0RzIfqEK5OlyFAzjUVlcqEVoKlBVUoLIysmMpEzhsPvkGeyQqErXoBMC1NJzGo-JjeHu13wn1uMfbnx2-AGyzIVacHzIpdioG4PlA4-xoB12QXbqrArGZTfMZaPsJz9xPg2wFcHOER95P5iHvTr__SyMzXfA36gfA8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2428378764</pqid></control><display><type>article</type><title>Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts</title><source>Royal Society of Chemistry</source><creator>Li, Feng ; Huang, Zhen-jie ; Zhou, Qian-hua ; Pan, Ming-yue ; Tang, Qian ; Gong, Cheng-bin</creator><creatorcontrib>Li, Feng ; Huang, Zhen-jie ; Zhou, Qian-hua ; Pan, Ming-yue ; Tang, Qian ; Gong, Cheng-bin</creatorcontrib><description>Developing electrochromic materials with energy-saving (
i.e.
, low driving voltage) and long-life (
i.e.
, high switching stability) properties is highly desirable with respect to practical application. In this work, we report the synthesis of two
N
,
N
′-di(4-pyridyl)-1,4,5,8-naphthalene diimide derivatives (DPNDIs), (Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br), and the characterization of their electrochemical and electrochromic properties. Both DPNDIs showed two quasi-reversible redox couples in the cyclic voltammograms with cathodic peak potentials of approximately −0.30 and −0.70 V
vs.
Ag/Ag
+
. The electrochromic devices based on ((Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br)) gave a colored state of dark orange and orange, respectively, which are colored states that have rarely been reported, and both DPNDIs had a low onset bias of −0.7 V and good switching stabilities (the change in optical contrast after 7200 s of <4%). The introduction of pyridinium salts at the DPNDI core enhanced its solubility and switching stability. In combination with density functional theory (DFT) calculations, it was shown that the formation of pyridinium salts modified the electronic properties of 1,4,5,8-naphthalenetetracarboxylic dianhydride (NDA) and DPNDI, and both pyridinium salt and NDA units contributed to electrochemical reduction. The results demonstrate that (Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br) are promising electrochromic materials and can be used in energy-saving buildings, smart windows, traffic signs, electronic paper, sunglasses, and anti-glare rearview mirrors.
Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts were developed.</description><identifier>ISSN: 2050-7526</identifier><identifier>EISSN: 2050-7534</identifier><identifier>DOI: 10.1039/d0tc00250j</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chemical reduction ; Density functional theory ; Dianhydrides ; Diimide ; Electrochemical analysis ; Electrochromic cells ; Electrochromism ; Electronic paper ; Energy conservation ; Naphthalene ; Properties (attributes) ; Smart materials ; Stability ; Sunglasses ; Switching ; Synthesis ; Traffic signs ; Windows (apertures)</subject><ispartof>Journal of materials chemistry. C, Materials for optical and electronic devices, 2020-08, Vol.8 (29), p.131-138</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c344t-3ad52e1ec1ce8bd74ca0edf0abac4d6b1454711e0080756be4cb380628db6e5f3</citedby><cites>FETCH-LOGICAL-c344t-3ad52e1ec1ce8bd74ca0edf0abac4d6b1454711e0080756be4cb380628db6e5f3</cites><orcidid>0000-0002-6947-1463</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></links><search><creatorcontrib>Li, Feng</creatorcontrib><creatorcontrib>Huang, Zhen-jie</creatorcontrib><creatorcontrib>Zhou, Qian-hua</creatorcontrib><creatorcontrib>Pan, Ming-yue</creatorcontrib><creatorcontrib>Tang, Qian</creatorcontrib><creatorcontrib>Gong, Cheng-bin</creatorcontrib><title>Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts</title><title>Journal of materials chemistry. C, Materials for optical and electronic devices</title><description>Developing electrochromic materials with energy-saving (
i.e.
, low driving voltage) and long-life (
i.e.
, high switching stability) properties is highly desirable with respect to practical application. In this work, we report the synthesis of two
N
,
N
′-di(4-pyridyl)-1,4,5,8-naphthalene diimide derivatives (DPNDIs), (Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br), and the characterization of their electrochemical and electrochromic properties. Both DPNDIs showed two quasi-reversible redox couples in the cyclic voltammograms with cathodic peak potentials of approximately −0.30 and −0.70 V
vs.
Ag/Ag
+
. The electrochromic devices based on ((Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br)) gave a colored state of dark orange and orange, respectively, which are colored states that have rarely been reported, and both DPNDIs had a low onset bias of −0.7 V and good switching stabilities (the change in optical contrast after 7200 s of <4%). The introduction of pyridinium salts at the DPNDI core enhanced its solubility and switching stability. In combination with density functional theory (DFT) calculations, it was shown that the formation of pyridinium salts modified the electronic properties of 1,4,5,8-naphthalenetetracarboxylic dianhydride (NDA) and DPNDI, and both pyridinium salt and NDA units contributed to electrochemical reduction. The results demonstrate that (Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br) are promising electrochromic materials and can be used in energy-saving buildings, smart windows, traffic signs, electronic paper, sunglasses, and anti-glare rearview mirrors.
Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts were developed.</description><subject>Chemical reduction</subject><subject>Density functional theory</subject><subject>Dianhydrides</subject><subject>Diimide</subject><subject>Electrochemical analysis</subject><subject>Electrochromic cells</subject><subject>Electrochromism</subject><subject>Electronic paper</subject><subject>Energy conservation</subject><subject>Naphthalene</subject><subject>Properties (attributes)</subject><subject>Smart materials</subject><subject>Stability</subject><subject>Sunglasses</subject><subject>Switching</subject><subject>Synthesis</subject><subject>Traffic signs</subject><subject>Windows (apertures)</subject><issn>2050-7526</issn><issn>2050-7534</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kM1LAzEQxYMoWGov3oWIN2F1sslmt0ep9YuCl3pesslsm7KbrMlW6H_f1Uq9OZcZeL-ZNzxCLhncMeDTewO9Bkgz2JyQUQoZJHnGxelxTuU5mcS4gaEKJgs5HZFq7jCsdklUX9atqHKGNt6tksbWSLFB3Qev18G3VtNW9RisaiL1NXWqW_dr1aBDaqxtrcFE-4CGdrtgjXV229Komj5ekLN6WMLJbx-Tj6f5cvaSLN6fX2cPi0RzIfqEK5OlyFAzjUVlcqEVoKlBVUoLIysmMpEzhsPvkGeyQqErXoBMC1NJzGo-JjeHu13wn1uMfbnx2-AGyzIVacHzIpdioG4PlA4-xoB12QXbqrArGZTfMZaPsJz9xPg2wFcHOER95P5iHvTr__SyMzXfA36gfA8</recordid><startdate>20200807</startdate><enddate>20200807</enddate><creator>Li, Feng</creator><creator>Huang, Zhen-jie</creator><creator>Zhou, Qian-hua</creator><creator>Pan, Ming-yue</creator><creator>Tang, Qian</creator><creator>Gong, Cheng-bin</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SP</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-6947-1463</orcidid></search><sort><creationdate>20200807</creationdate><title>Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts</title><author>Li, Feng ; Huang, Zhen-jie ; Zhou, Qian-hua ; Pan, Ming-yue ; Tang, Qian ; Gong, Cheng-bin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c344t-3ad52e1ec1ce8bd74ca0edf0abac4d6b1454711e0080756be4cb380628db6e5f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemical reduction</topic><topic>Density functional theory</topic><topic>Dianhydrides</topic><topic>Diimide</topic><topic>Electrochemical analysis</topic><topic>Electrochromic cells</topic><topic>Electrochromism</topic><topic>Electronic paper</topic><topic>Energy conservation</topic><topic>Naphthalene</topic><topic>Properties (attributes)</topic><topic>Smart materials</topic><topic>Stability</topic><topic>Sunglasses</topic><topic>Switching</topic><topic>Synthesis</topic><topic>Traffic signs</topic><topic>Windows (apertures)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Feng</creatorcontrib><creatorcontrib>Huang, Zhen-jie</creatorcontrib><creatorcontrib>Zhou, Qian-hua</creatorcontrib><creatorcontrib>Pan, Ming-yue</creatorcontrib><creatorcontrib>Tang, Qian</creatorcontrib><creatorcontrib>Gong, Cheng-bin</creatorcontrib><collection>CrossRef</collection><collection>Electronics & Communications Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of materials chemistry. C, Materials for optical and electronic devices</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Feng</au><au>Huang, Zhen-jie</au><au>Zhou, Qian-hua</au><au>Pan, Ming-yue</au><au>Tang, Qian</au><au>Gong, Cheng-bin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts</atitle><jtitle>Journal of materials chemistry. C, Materials for optical and electronic devices</jtitle><date>2020-08-07</date><risdate>2020</risdate><volume>8</volume><issue>29</issue><spage>131</spage><epage>138</epage><pages>131-138</pages><issn>2050-7526</issn><eissn>2050-7534</eissn><abstract>Developing electrochromic materials with energy-saving (
i.e.
, low driving voltage) and long-life (
i.e.
, high switching stability) properties is highly desirable with respect to practical application. In this work, we report the synthesis of two
N
,
N
′-di(4-pyridyl)-1,4,5,8-naphthalene diimide derivatives (DPNDIs), (Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br), and the characterization of their electrochemical and electrochromic properties. Both DPNDIs showed two quasi-reversible redox couples in the cyclic voltammograms with cathodic peak potentials of approximately −0.30 and −0.70 V
vs.
Ag/Ag
+
. The electrochromic devices based on ((Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br)) gave a colored state of dark orange and orange, respectively, which are colored states that have rarely been reported, and both DPNDIs had a low onset bias of −0.7 V and good switching stabilities (the change in optical contrast after 7200 s of <4%). The introduction of pyridinium salts at the DPNDI core enhanced its solubility and switching stability. In combination with density functional theory (DFT) calculations, it was shown that the formation of pyridinium salts modified the electronic properties of 1,4,5,8-naphthalenetetracarboxylic dianhydride (NDA) and DPNDI, and both pyridinium salt and NDA units contributed to electrochemical reduction. The results demonstrate that (Me
2
DPNDI)·(2I) and (benzyl
2
DPNDI)·(2Br) are promising electrochromic materials and can be used in energy-saving buildings, smart windows, traffic signs, electronic paper, sunglasses, and anti-glare rearview mirrors.
Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts were developed.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0tc00250j</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-6947-1463</orcidid></addata></record> |
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| identifier | ISSN: 2050-7526 |
| ispartof | Journal of materials chemistry. C, Materials for optical and electronic devices, 2020-08, Vol.8 (29), p.131-138 |
| issn | 2050-7526 2050-7534 |
| language | eng |
| recordid | cdi_proquest_journals_2428378764 |
| source | Royal Society of Chemistry |
| subjects | Chemical reduction Density functional theory Dianhydrides Diimide Electrochemical analysis Electrochromic cells Electrochromism Electronic paper Energy conservation Naphthalene Properties (attributes) Smart materials Stability Sunglasses Switching Synthesis Traffic signs Windows (apertures) |
| title | Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts |
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