Azapyrene-based fluorophores: synthesis and photophysical properties
Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron-acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of "push-pull" π-conjugated chromophores with pronounced ICT properties. Over the p...
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| Veröffentlicht in: | New journal of chemistry 2021-11, Vol.45 (45), p.2955-2971 |
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| creator | Taniya, Olga S Khasanov, Albert F Varaksin, Mikhail V Starnovskaya, Ekaterina S Krinochkin, Alexey P Savchuk, Maria I Kopchuk, Dmitry S Kovalev, Igor S Kim, Grigory A Nosova, Emiliya V Zyryanov, Grigory V Chupakhin, Oleg N |
| description | Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron-acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of "push-pull" π-conjugated chromophores with pronounced ICT properties. Over the past decade, due to the unrelenting interest in functional materials and modern methodologies such as cross-coupling,
peri
-annulation, direct C-H-functionalization,
etc.
, methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene.
The latest methods for the preparation/functionalization of azapyrenes, and their photophysical/electrochemical properties and possible applications are overviewed. |
| doi_str_mv | 10.1039/d1nj03531b |
| format | Article |
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peri
-annulation, direct C-H-functionalization,
etc.
, methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene.
The latest methods for the preparation/functionalization of azapyrenes, and their photophysical/electrochemical properties and possible applications are overviewed.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d1nj03531b</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chemical compounds ; Chemical reactions ; Chromophores ; Cross coupling ; Electrochemical analysis ; Fluorescence ; Functional materials ; Synthesis</subject><ispartof>New journal of chemistry, 2021-11, Vol.45 (45), p.2955-2971</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-7b54c82b584aaba749d01d73cd6c152764e74998e4010402da96a1cd9e7fc2523</citedby><cites>FETCH-LOGICAL-c281t-7b54c82b584aaba749d01d73cd6c152764e74998e4010402da96a1cd9e7fc2523</cites><orcidid>0000-0002-7997-3686 ; 0000-0002-0537-3274 ; 0000-0002-1672-2476 ; 0000-0002-0177-1582</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Taniya, Olga S</creatorcontrib><creatorcontrib>Khasanov, Albert F</creatorcontrib><creatorcontrib>Varaksin, Mikhail V</creatorcontrib><creatorcontrib>Starnovskaya, Ekaterina S</creatorcontrib><creatorcontrib>Krinochkin, Alexey P</creatorcontrib><creatorcontrib>Savchuk, Maria I</creatorcontrib><creatorcontrib>Kopchuk, Dmitry S</creatorcontrib><creatorcontrib>Kovalev, Igor S</creatorcontrib><creatorcontrib>Kim, Grigory A</creatorcontrib><creatorcontrib>Nosova, Emiliya V</creatorcontrib><creatorcontrib>Zyryanov, Grigory V</creatorcontrib><creatorcontrib>Chupakhin, Oleg N</creatorcontrib><title>Azapyrene-based fluorophores: synthesis and photophysical properties</title><title>New journal of chemistry</title><description>Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron-acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of "push-pull" π-conjugated chromophores with pronounced ICT properties. Over the past decade, due to the unrelenting interest in functional materials and modern methodologies such as cross-coupling,
peri
-annulation, direct C-H-functionalization,
etc.
, methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene.
The latest methods for the preparation/functionalization of azapyrenes, and their photophysical/electrochemical properties and possible applications are overviewed.</description><subject>Chemical compounds</subject><subject>Chemical reactions</subject><subject>Chromophores</subject><subject>Cross coupling</subject><subject>Electrochemical analysis</subject><subject>Fluorescence</subject><subject>Functional materials</subject><subject>Synthesis</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFkE1LxDAQhoMouK5evAsFb0J1JknTxtu66yeLXvRc0iRlu6xtzXQP9dcbXdHTDO88zAsPY6cIlwhCXzls1yAygdUem6BQOtVc4X7cUcoUMqkO2RHRGgAxVzhhi9mn6cfgW59WhrxL6s22C12_6oKn64TGdlh5aigxrUtiOsTTSI01m6SPmA9D4-mYHdRmQ_7kd07Z293t6_whXb7cP85ny9TyAoc0rzJpC15lhTSmMrnUDtDlwjplMeO5kj5muvASECRwZ7QyaJ32eW15xsWUne_-xuqPraehXHfb0MbKkivAQkgBMlIXO8qGjij4uuxD827CWCKU35bKBT4__Vi6ifDZDg5k_7h_i-ILFipkEQ</recordid><startdate>20211122</startdate><enddate>20211122</enddate><creator>Taniya, Olga S</creator><creator>Khasanov, Albert F</creator><creator>Varaksin, Mikhail V</creator><creator>Starnovskaya, Ekaterina S</creator><creator>Krinochkin, Alexey P</creator><creator>Savchuk, Maria I</creator><creator>Kopchuk, Dmitry S</creator><creator>Kovalev, Igor S</creator><creator>Kim, Grigory A</creator><creator>Nosova, Emiliya V</creator><creator>Zyryanov, Grigory V</creator><creator>Chupakhin, Oleg N</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0002-7997-3686</orcidid><orcidid>https://orcid.org/0000-0002-0537-3274</orcidid><orcidid>https://orcid.org/0000-0002-1672-2476</orcidid><orcidid>https://orcid.org/0000-0002-0177-1582</orcidid></search><sort><creationdate>20211122</creationdate><title>Azapyrene-based fluorophores: synthesis and photophysical properties</title><author>Taniya, Olga S ; Khasanov, Albert F ; Varaksin, Mikhail V ; Starnovskaya, Ekaterina S ; Krinochkin, Alexey P ; Savchuk, Maria I ; Kopchuk, Dmitry S ; Kovalev, Igor S ; Kim, Grigory A ; Nosova, Emiliya V ; Zyryanov, Grigory V ; Chupakhin, Oleg N</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-7b54c82b584aaba749d01d73cd6c152764e74998e4010402da96a1cd9e7fc2523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemical compounds</topic><topic>Chemical reactions</topic><topic>Chromophores</topic><topic>Cross coupling</topic><topic>Electrochemical analysis</topic><topic>Fluorescence</topic><topic>Functional materials</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Taniya, Olga S</creatorcontrib><creatorcontrib>Khasanov, Albert F</creatorcontrib><creatorcontrib>Varaksin, Mikhail V</creatorcontrib><creatorcontrib>Starnovskaya, Ekaterina S</creatorcontrib><creatorcontrib>Krinochkin, Alexey P</creatorcontrib><creatorcontrib>Savchuk, Maria I</creatorcontrib><creatorcontrib>Kopchuk, Dmitry S</creatorcontrib><creatorcontrib>Kovalev, Igor S</creatorcontrib><creatorcontrib>Kim, Grigory A</creatorcontrib><creatorcontrib>Nosova, Emiliya V</creatorcontrib><creatorcontrib>Zyryanov, Grigory V</creatorcontrib><creatorcontrib>Chupakhin, Oleg N</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taniya, Olga S</au><au>Khasanov, Albert F</au><au>Varaksin, Mikhail V</au><au>Starnovskaya, Ekaterina S</au><au>Krinochkin, Alexey P</au><au>Savchuk, Maria I</au><au>Kopchuk, Dmitry S</au><au>Kovalev, Igor S</au><au>Kim, Grigory A</au><au>Nosova, Emiliya V</au><au>Zyryanov, Grigory V</au><au>Chupakhin, Oleg N</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Azapyrene-based fluorophores: synthesis and photophysical properties</atitle><jtitle>New journal of chemistry</jtitle><date>2021-11-22</date><risdate>2021</risdate><volume>45</volume><issue>45</issue><spage>2955</spage><epage>2971</epage><pages>2955-2971</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron-acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of "push-pull" π-conjugated chromophores with pronounced ICT properties. Over the past decade, due to the unrelenting interest in functional materials and modern methodologies such as cross-coupling,
peri
-annulation, direct C-H-functionalization,
etc.
, methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene.
The latest methods for the preparation/functionalization of azapyrenes, and their photophysical/electrochemical properties and possible applications are overviewed.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1nj03531b</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0002-7997-3686</orcidid><orcidid>https://orcid.org/0000-0002-0537-3274</orcidid><orcidid>https://orcid.org/0000-0002-1672-2476</orcidid><orcidid>https://orcid.org/0000-0002-0177-1582</orcidid></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical compounds Chemical reactions Chromophores Cross coupling Electrochemical analysis Fluorescence Functional materials Synthesis |
| title | Azapyrene-based fluorophores: synthesis and photophysical properties |
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