A new MediaChrom (fluorosolvatochromic and acidochromic) based on bipolar donor-acceptor conjoined carbazolo-phenazine
[Display omitted] •Carbazolo-phenazine CP is a new conjoined bipolar MediaChrome.•CP exhibits fluorosolvatochromism as result of ICT in the excited state.•The dipole moment difference in the ground and excited states is 3.6 D.•Protonation of CP leads to violet coloration due to ICT in the ground sta...
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| Veröffentlicht in: | Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2017-10, Vol.347, p.199-208 |
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| container_title | Journal of photochemistry and photobiology. A, Chemistry. |
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| creator | Mukhopadhyay, Arindam Mishra, Abhaya Kumar Jana, Kanyashree Moorthy, Jarugu Narasimha |
| description | [Display omitted]
•Carbazolo-phenazine CP is a new conjoined bipolar MediaChrome.•CP exhibits fluorosolvatochromism as result of ICT in the excited state.•The dipole moment difference in the ground and excited states is 3.6 D.•Protonation of CP leads to violet coloration due to ICT in the ground state.
MediaChromes are molecular systems characterized by a rigid aromatic backbone bearing electron-donating (D) and accepting (A) groups conjugated in the so-called push-pull D–π–A fashion. Electronic excitation of such systems results in increase of the dipole moment in the excited state due to intramolecular charge transfer (ICT), leading to remarkable excited-state properties. We have investigated fluorosolvatochromic and halochromic (acidochromic) behavior of carbazolo-phenazine (CP), a new bipolar molecular system characterized by conjoined donor carbazole and acceptor phenazine heterocycles. CP is shown to exhibit exceptional fluoromediachromic behavior due to ICT in the excited state; the difference in the dipole moments of ground- and singlet-excited states of CP is ca. 3.6 D units. ICT occurs also in the ground state upon protonation, which manifests in brilliant naked-eye visible violet coloration, namely, acidochromism. |
| doi_str_mv | 10.1016/j.jphotochem.2017.07.041 |
| format | Article |
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•Carbazolo-phenazine CP is a new conjoined bipolar MediaChrome.•CP exhibits fluorosolvatochromism as result of ICT in the excited state.•The dipole moment difference in the ground and excited states is 3.6 D.•Protonation of CP leads to violet coloration due to ICT in the ground state.
MediaChromes are molecular systems characterized by a rigid aromatic backbone bearing electron-donating (D) and accepting (A) groups conjugated in the so-called push-pull D–π–A fashion. Electronic excitation of such systems results in increase of the dipole moment in the excited state due to intramolecular charge transfer (ICT), leading to remarkable excited-state properties. We have investigated fluorosolvatochromic and halochromic (acidochromic) behavior of carbazolo-phenazine (CP), a new bipolar molecular system characterized by conjoined donor carbazole and acceptor phenazine heterocycles. CP is shown to exhibit exceptional fluoromediachromic behavior due to ICT in the excited state; the difference in the dipole moments of ground- and singlet-excited states of CP is ca. 3.6 D units. ICT occurs also in the ground state upon protonation, which manifests in brilliant naked-eye visible violet coloration, namely, acidochromism.</description><identifier>ISSN: 1010-6030</identifier><identifier>EISSN: 1873-2666</identifier><identifier>DOI: 10.1016/j.jphotochem.2017.07.041</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>Acidochromism ; Carbazole ; Charge transfer ; Chemical elements ; Coloration ; Dipole moments ; Electrons ; Excitation ; Fluorescence ; Phenazine ; Protonation ; Solvatochromism ; Studies</subject><ispartof>Journal of photochemistry and photobiology. A, Chemistry., 2017-10, Vol.347, p.199-208</ispartof><rights>2017 Elsevier B.V.</rights><rights>Copyright Elsevier BV Oct 1, 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-7d825f8cb39eb424753875e7b974273e367b9783911c42856d601910382b61993</citedby><cites>FETCH-LOGICAL-c412t-7d825f8cb39eb424753875e7b974273e367b9783911c42856d601910382b61993</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jphotochem.2017.07.041$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids></links><search><creatorcontrib>Mukhopadhyay, Arindam</creatorcontrib><creatorcontrib>Mishra, Abhaya Kumar</creatorcontrib><creatorcontrib>Jana, Kanyashree</creatorcontrib><creatorcontrib>Moorthy, Jarugu Narasimha</creatorcontrib><title>A new MediaChrom (fluorosolvatochromic and acidochromic) based on bipolar donor-acceptor conjoined carbazolo-phenazine</title><title>Journal of photochemistry and photobiology. A, Chemistry.</title><description>[Display omitted]
•Carbazolo-phenazine CP is a new conjoined bipolar MediaChrome.•CP exhibits fluorosolvatochromism as result of ICT in the excited state.•The dipole moment difference in the ground and excited states is 3.6 D.•Protonation of CP leads to violet coloration due to ICT in the ground state.
MediaChromes are molecular systems characterized by a rigid aromatic backbone bearing electron-donating (D) and accepting (A) groups conjugated in the so-called push-pull D–π–A fashion. Electronic excitation of such systems results in increase of the dipole moment in the excited state due to intramolecular charge transfer (ICT), leading to remarkable excited-state properties. We have investigated fluorosolvatochromic and halochromic (acidochromic) behavior of carbazolo-phenazine (CP), a new bipolar molecular system characterized by conjoined donor carbazole and acceptor phenazine heterocycles. CP is shown to exhibit exceptional fluoromediachromic behavior due to ICT in the excited state; the difference in the dipole moments of ground- and singlet-excited states of CP is ca. 3.6 D units. ICT occurs also in the ground state upon protonation, which manifests in brilliant naked-eye visible violet coloration, namely, acidochromism.</description><subject>Acidochromism</subject><subject>Carbazole</subject><subject>Charge transfer</subject><subject>Chemical elements</subject><subject>Coloration</subject><subject>Dipole moments</subject><subject>Electrons</subject><subject>Excitation</subject><subject>Fluorescence</subject><subject>Phenazine</subject><subject>Protonation</subject><subject>Solvatochromism</subject><subject>Studies</subject><issn>1010-6030</issn><issn>1873-2666</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFUE1LAzEUDKKgVv9DwIsetuYlaTZ71OIXKF70HLLZlGbZ5q3ZbcX-elOqeBQG3mOYmccbQiiwKTBQ1-207Zc4olv61ZQzKKcsQ8IBOQFdioIrpQ7zzoAVigl2TE6HoWWMSSnhhGxuaPSf9MU3wc6XCVf0ctGtMeGA3cbuYjMXHLWxodaF5pe4orUdfEMx0jr02NlEG4yYCuuc70dM1GFsMcSscTbVdosdFv3SR7vN5Bk5Wthu8Oc_c0Le7-_e5o_F8-vD0_zmuXAS-FiUjeazhXa1qHwtuSxnQpczX9ZVKXkpvFC7VYsKwEmuZ6pRDCpgQvNaQVWJCbnY5_YJP9Z-GE2L6xTzSQOVYpUWPOdMiN6rXP57SH5h-hRWNn0ZYGbXsmnNX8tm17JhGRKy9XZv9fmLTfDJDC746HKfybvRNBj-D_kGrlSLfA</recordid><startdate>20171001</startdate><enddate>20171001</enddate><creator>Mukhopadhyay, Arindam</creator><creator>Mishra, Abhaya Kumar</creator><creator>Jana, Kanyashree</creator><creator>Moorthy, Jarugu Narasimha</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20171001</creationdate><title>A new MediaChrom (fluorosolvatochromic and acidochromic) based on bipolar donor-acceptor conjoined carbazolo-phenazine</title><author>Mukhopadhyay, Arindam ; Mishra, Abhaya Kumar ; Jana, Kanyashree ; Moorthy, Jarugu Narasimha</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-7d825f8cb39eb424753875e7b974273e367b9783911c42856d601910382b61993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acidochromism</topic><topic>Carbazole</topic><topic>Charge transfer</topic><topic>Chemical elements</topic><topic>Coloration</topic><topic>Dipole moments</topic><topic>Electrons</topic><topic>Excitation</topic><topic>Fluorescence</topic><topic>Phenazine</topic><topic>Protonation</topic><topic>Solvatochromism</topic><topic>Studies</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mukhopadhyay, Arindam</creatorcontrib><creatorcontrib>Mishra, Abhaya Kumar</creatorcontrib><creatorcontrib>Jana, Kanyashree</creatorcontrib><creatorcontrib>Moorthy, Jarugu Narasimha</creatorcontrib><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of photochemistry and photobiology. A, Chemistry.</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mukhopadhyay, Arindam</au><au>Mishra, Abhaya Kumar</au><au>Jana, Kanyashree</au><au>Moorthy, Jarugu Narasimha</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new MediaChrom (fluorosolvatochromic and acidochromic) based on bipolar donor-acceptor conjoined carbazolo-phenazine</atitle><jtitle>Journal of photochemistry and photobiology. A, Chemistry.</jtitle><date>2017-10-01</date><risdate>2017</risdate><volume>347</volume><spage>199</spage><epage>208</epage><pages>199-208</pages><issn>1010-6030</issn><eissn>1873-2666</eissn><abstract>[Display omitted]
•Carbazolo-phenazine CP is a new conjoined bipolar MediaChrome.•CP exhibits fluorosolvatochromism as result of ICT in the excited state.•The dipole moment difference in the ground and excited states is 3.6 D.•Protonation of CP leads to violet coloration due to ICT in the ground state.
MediaChromes are molecular systems characterized by a rigid aromatic backbone bearing electron-donating (D) and accepting (A) groups conjugated in the so-called push-pull D–π–A fashion. Electronic excitation of such systems results in increase of the dipole moment in the excited state due to intramolecular charge transfer (ICT), leading to remarkable excited-state properties. We have investigated fluorosolvatochromic and halochromic (acidochromic) behavior of carbazolo-phenazine (CP), a new bipolar molecular system characterized by conjoined donor carbazole and acceptor phenazine heterocycles. CP is shown to exhibit exceptional fluoromediachromic behavior due to ICT in the excited state; the difference in the dipole moments of ground- and singlet-excited states of CP is ca. 3.6 D units. ICT occurs also in the ground state upon protonation, which manifests in brilliant naked-eye visible violet coloration, namely, acidochromism.</abstract><cop>Lausanne</cop><pub>Elsevier B.V</pub><doi>10.1016/j.jphotochem.2017.07.041</doi><tpages>10</tpages></addata></record> |
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| subjects | Acidochromism Carbazole Charge transfer Chemical elements Coloration Dipole moments Electrons Excitation Fluorescence Phenazine Protonation Solvatochromism Studies |
| title | A new MediaChrom (fluorosolvatochromic and acidochromic) based on bipolar donor-acceptor conjoined carbazolo-phenazine |
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