New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety
New D-π-A-type chromophores that simultaneously incorporate N,N -dimethylaminophenyl moiety as the terminal electron-donating group and either (5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile (DCM-1) or (6-methyl-4 H -pyran-4-ylidene)malononitrile (DCM-2) unit as the terminal electron-withdrawing...
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| Veröffentlicht in: | Russian chemical bulletin 2022-02, Vol.71 (2), p.341-349 |
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| container_title | Russian chemical bulletin |
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| creator | Slobodinyuk, D. G. Vasyanin, A. N. Lunegov, I. V. Sklyaeva, E. V. Abashev, G. G. |
| description | New D-π-A-type chromophores that simultaneously incorporate
N,N
-dimethylaminophenyl moiety as the terminal electron-donating group and either (5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile (DCM-1) or (6-methyl-4
H
-pyran-4-ylidene)malononitrile (DCM-2) unit as the terminal electron-withdrawing group were synthesized. Vinylene moiety and azo group served as the π-spacer. A comparative analysis of optical and electrochemical properties of the synthesized chromophores revealed that the replacement of the DCM-1 unit with the DCM-2 moiety led to chromophore band gap broadening and a decrease in the molar extinction coefficient value; while the replacement of the DCM-1 unit with the DCM-2 one in the chromophores bearing the vinylene π-spacers led to a sharp increase in the fluorescence quantum yield. |
| doi_str_mv | 10.1007/s11172-022-3417-2 |
| format | Article |
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N,N
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H
-pyran-4-ylidene)malononitrile (DCM-2) unit as the terminal electron-withdrawing group were synthesized. Vinylene moiety and azo group served as the π-spacer. A comparative analysis of optical and electrochemical properties of the synthesized chromophores revealed that the replacement of the DCM-1 unit with the DCM-2 moiety led to chromophore band gap broadening and a decrease in the molar extinction coefficient value; while the replacement of the DCM-1 unit with the DCM-2 one in the chromophores bearing the vinylene π-spacers led to a sharp increase in the fluorescence quantum yield.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-022-3417-2</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Chromophores ; Electrochemical analysis ; Full Articles ; Inorganic Chemistry ; Malononitrile ; Optical properties ; Organic Chemistry ; Synthesis</subject><ispartof>Russian chemical bulletin, 2022-02, Vol.71 (2), p.341-349</ispartof><rights>Springer Science+Business Media LLC 2022</rights><rights>Springer Science+Business Media LLC 2022.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c246t-162c5f8bee12c4fe90c19acb24a4ebaff4f01fcc875c25c50aedf06691389d803</citedby><cites>FETCH-LOGICAL-c246t-162c5f8bee12c4fe90c19acb24a4ebaff4f01fcc875c25c50aedf06691389d803</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-022-3417-2$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-022-3417-2$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Slobodinyuk, D. G.</creatorcontrib><creatorcontrib>Vasyanin, A. N.</creatorcontrib><creatorcontrib>Lunegov, I. V.</creatorcontrib><creatorcontrib>Sklyaeva, E. V.</creatorcontrib><creatorcontrib>Abashev, G. G.</creatorcontrib><title>New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>New D-π-A-type chromophores that simultaneously incorporate
N,N
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H
-pyran-4-ylidene)malononitrile (DCM-2) unit as the terminal electron-withdrawing group were synthesized. Vinylene moiety and azo group served as the π-spacer. A comparative analysis of optical and electrochemical properties of the synthesized chromophores revealed that the replacement of the DCM-1 unit with the DCM-2 moiety led to chromophore band gap broadening and a decrease in the molar extinction coefficient value; while the replacement of the DCM-1 unit with the DCM-2 one in the chromophores bearing the vinylene π-spacers led to a sharp increase in the fluorescence quantum yield.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Chromophores</subject><subject>Electrochemical analysis</subject><subject>Full Articles</subject><subject>Inorganic Chemistry</subject><subject>Malononitrile</subject><subject>Optical properties</subject><subject>Organic Chemistry</subject><subject>Synthesis</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LxDAQhosouK7-AG8FLwqOZtKmH0fxawXRi55DNjvZ7dImNalob-If9C_ZpcKePM0cnvcd5omiY2QXyFh-GRAx58A4hyTFHPhONEGRJ1BijrvDzrIMBC_EfnQQwpoxxouimETfT_QR38DPF1zFeuVd49qV8xTiymrnW-dVV9llfCrOBSyqhrpVX-te125Fn8CBLCD0dbUgS2cQOx-fZjBSkM6g7b2ykG6JRtXOOlt1vqopblxFXX8Y7RlVBzr6m9Po9e725XoGj8_3D9dXj6B5mnWAGdfCFHMi5Do1VDKNpdJznqqU5sqY1DA0Whe50FxowRQtzPB1iUlRLgqWTKOTsbf17u2dQifX7t3b4aTkmUh4mSUJDhSOlPYuBE9Gtr5qlO8lMrlRLUfVclAtN6olHzJ8zISBtUvy2-b_Q79KfoHg</recordid><startdate>20220201</startdate><enddate>20220201</enddate><creator>Slobodinyuk, D. G.</creator><creator>Vasyanin, A. N.</creator><creator>Lunegov, I. V.</creator><creator>Sklyaeva, E. V.</creator><creator>Abashev, G. G.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20220201</creationdate><title>New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety</title><author>Slobodinyuk, D. G. ; Vasyanin, A. N. ; Lunegov, I. V. ; Sklyaeva, E. V. ; Abashev, G. G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c246t-162c5f8bee12c4fe90c19acb24a4ebaff4f01fcc875c25c50aedf06691389d803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Chromophores</topic><topic>Electrochemical analysis</topic><topic>Full Articles</topic><topic>Inorganic Chemistry</topic><topic>Malononitrile</topic><topic>Optical properties</topic><topic>Organic Chemistry</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Slobodinyuk, D. G.</creatorcontrib><creatorcontrib>Vasyanin, A. N.</creatorcontrib><creatorcontrib>Lunegov, I. V.</creatorcontrib><creatorcontrib>Sklyaeva, E. V.</creatorcontrib><creatorcontrib>Abashev, G. G.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Slobodinyuk, D. G.</au><au>Vasyanin, A. N.</au><au>Lunegov, I. V.</au><au>Sklyaeva, E. V.</au><au>Abashev, G. G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2022-02-01</date><risdate>2022</risdate><volume>71</volume><issue>2</issue><spage>341</spage><epage>349</epage><pages>341-349</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>New D-π-A-type chromophores that simultaneously incorporate
N,N
-dimethylaminophenyl moiety as the terminal electron-donating group and either (5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile (DCM-1) or (6-methyl-4
H
-pyran-4-ylidene)malononitrile (DCM-2) unit as the terminal electron-withdrawing group were synthesized. Vinylene moiety and azo group served as the π-spacer. A comparative analysis of optical and electrochemical properties of the synthesized chromophores revealed that the replacement of the DCM-1 unit with the DCM-2 moiety led to chromophore band gap broadening and a decrease in the molar extinction coefficient value; while the replacement of the DCM-1 unit with the DCM-2 one in the chromophores bearing the vinylene π-spacers led to a sharp increase in the fluorescence quantum yield.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-022-3417-2</doi><tpages>9</tpages></addata></record> |
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| language | eng |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Chemistry Chemistry and Materials Science Chemistry/Food Science Chromophores Electrochemical analysis Full Articles Inorganic Chemistry Malononitrile Optical properties Organic Chemistry Synthesis |
| title | New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety |
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