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On the synthesis, optical and computational studies of novel BODIPY-based phosphoramidate fluorescent dyes
New BODIPY fluorophores substituted with phosphoramidate groups have been synthesized and their photophysical properties were evaluated in details. [Display omitted] •Novel fluorescent probe based on the integration of aminoalkylphosphoramidate and BODIPY was designed.•Compounds were synthesized, we...
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| Published in: | Journal of fluorine chemistry 2019-04, Vol.220, p.9-15 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c340t-fe729630c33b00a969799975adfb557359ba6af1ef01a60ce02e3b60131c3f93 |
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| cites | cdi_FETCH-LOGICAL-c340t-fe729630c33b00a969799975adfb557359ba6af1ef01a60ce02e3b60131c3f93 |
| container_end_page | 15 |
| container_issue | |
| container_start_page | 9 |
| container_title | Journal of fluorine chemistry |
| container_volume | 220 |
| creator | Machado, Luana A. de Souza, Marcos C. da Silva, Caroline M. Yoneda, Julliane de Rezende, Lucas C.D. Emery, Flavio S. de Simone, Carlos A. da Silva Júnior, Eufrânio N. Pedrosa, Leandro F. |
| description | New BODIPY fluorophores substituted with phosphoramidate groups have been synthesized and their photophysical properties were evaluated in details.
[Display omitted]
•Novel fluorescent probe based on the integration of aminoalkylphosphoramidate and BODIPY was designed.•Compounds were synthesized, well-characterized and their photophysical properties were investigated.•The BODIPY-based phosphoramidate derivatives containing fluorine are photostable with high absorption and emission in organic solvents.
New boro-dipyrromethene (BODIPY) fluorophores substituted with phosphoramidate groups have been synthesized using environmentally friendly methodologies, and their photophysical properties were evaluated experimentally and characterized in detail with respect to DFT and TD-DFT using B3LYP/6-31+G(d) level of theory. These fluorophores may be used as promising candidates for biological probes and optical materials. |
| doi_str_mv | 10.1016/j.jfluchem.2019.01.008 |
| format | article |
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[Display omitted]
•Novel fluorescent probe based on the integration of aminoalkylphosphoramidate and BODIPY was designed.•Compounds were synthesized, well-characterized and their photophysical properties were investigated.•The BODIPY-based phosphoramidate derivatives containing fluorine are photostable with high absorption and emission in organic solvents.
New boro-dipyrromethene (BODIPY) fluorophores substituted with phosphoramidate groups have been synthesized using environmentally friendly methodologies, and their photophysical properties were evaluated experimentally and characterized in detail with respect to DFT and TD-DFT using B3LYP/6-31+G(d) level of theory. These fluorophores may be used as promising candidates for biological probes and optical materials.</description><identifier>ISSN: 0022-1139</identifier><identifier>EISSN: 1873-3328</identifier><identifier>DOI: 10.1016/j.jfluchem.2019.01.008</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>Biological materials ; BODIPY ; Chemical compounds ; Computational studies ; Computer applications ; Fluorescence ; Fluorescent dyes ; Fluorescent indicators ; Fluorophores ; Optical materials ; Optics ; Phosphoramidates</subject><ispartof>Journal of fluorine chemistry, 2019-04, Vol.220, p.9-15</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright Elsevier BV Apr 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c340t-fe729630c33b00a969799975adfb557359ba6af1ef01a60ce02e3b60131c3f93</citedby><cites>FETCH-LOGICAL-c340t-fe729630c33b00a969799975adfb557359ba6af1ef01a60ce02e3b60131c3f93</cites><orcidid>0000-0002-2957-2307 ; 0000-0003-2428-0396</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Machado, Luana A.</creatorcontrib><creatorcontrib>de Souza, Marcos C.</creatorcontrib><creatorcontrib>da Silva, Caroline M.</creatorcontrib><creatorcontrib>Yoneda, Julliane</creatorcontrib><creatorcontrib>de Rezende, Lucas C.D.</creatorcontrib><creatorcontrib>Emery, Flavio S.</creatorcontrib><creatorcontrib>de Simone, Carlos A.</creatorcontrib><creatorcontrib>da Silva Júnior, Eufrânio N.</creatorcontrib><creatorcontrib>Pedrosa, Leandro F.</creatorcontrib><title>On the synthesis, optical and computational studies of novel BODIPY-based phosphoramidate fluorescent dyes</title><title>Journal of fluorine chemistry</title><description>New BODIPY fluorophores substituted with phosphoramidate groups have been synthesized and their photophysical properties were evaluated in details.
[Display omitted]
•Novel fluorescent probe based on the integration of aminoalkylphosphoramidate and BODIPY was designed.•Compounds were synthesized, well-characterized and their photophysical properties were investigated.•The BODIPY-based phosphoramidate derivatives containing fluorine are photostable with high absorption and emission in organic solvents.
New boro-dipyrromethene (BODIPY) fluorophores substituted with phosphoramidate groups have been synthesized using environmentally friendly methodologies, and their photophysical properties were evaluated experimentally and characterized in detail with respect to DFT and TD-DFT using B3LYP/6-31+G(d) level of theory. These fluorophores may be used as promising candidates for biological probes and optical materials.</description><subject>Biological materials</subject><subject>BODIPY</subject><subject>Chemical compounds</subject><subject>Computational studies</subject><subject>Computer applications</subject><subject>Fluorescence</subject><subject>Fluorescent dyes</subject><subject>Fluorescent indicators</subject><subject>Fluorophores</subject><subject>Optical materials</subject><subject>Optics</subject><subject>Phosphoramidates</subject><issn>0022-1139</issn><issn>1873-3328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkEFr3DAQhUVoINukfyEIeo2dkZS1rVubtE0Cgc0hl56ELI9YmV3L1ciB_fdR2OTcw_BgmPd48zF2KaAWIJrrsR79bnFb3NcShK5B1ADdCVuJrlWVUrL7wlYAUlZCKH3GvhKNANBC263YuJl43iKnw1SEAl3xOOfg7I7baeAu7ucl2xziVDaUlyEg8ej5FF9xx283vx6f_1a9JRz4vI1UJtl9GGxGXkrFhORwynw4IF2wU293hN8-9Jy9_Pn9cvdQPW3uH-9-PlVO3UCuPLZSNwqcUj2A1Y1utdbt2g6-X69btda9bawX6EHYBhyCRNU3IJRwymt1zr4fY-cU_y1I2YxxSaU-GSmlaLsbLZpy1RyvXIpECb2ZU9jbdDACzDtWM5pPrOYdqwFhCtZi_HE0YnnhNWAy5AJODoeQ0GUzxPC_iDflF4Ve</recordid><startdate>201904</startdate><enddate>201904</enddate><creator>Machado, Luana A.</creator><creator>de Souza, Marcos C.</creator><creator>da Silva, Caroline M.</creator><creator>Yoneda, Julliane</creator><creator>de Rezende, Lucas C.D.</creator><creator>Emery, Flavio S.</creator><creator>de Simone, Carlos A.</creator><creator>da Silva Júnior, Eufrânio N.</creator><creator>Pedrosa, Leandro F.</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-2957-2307</orcidid><orcidid>https://orcid.org/0000-0003-2428-0396</orcidid></search><sort><creationdate>201904</creationdate><title>On the synthesis, optical and computational studies of novel BODIPY-based phosphoramidate fluorescent dyes</title><author>Machado, Luana A. ; de Souza, Marcos C. ; da Silva, Caroline M. ; Yoneda, Julliane ; de Rezende, Lucas C.D. ; Emery, Flavio S. ; de Simone, Carlos A. ; da Silva Júnior, Eufrânio N. ; Pedrosa, Leandro F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c340t-fe729630c33b00a969799975adfb557359ba6af1ef01a60ce02e3b60131c3f93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Biological materials</topic><topic>BODIPY</topic><topic>Chemical compounds</topic><topic>Computational studies</topic><topic>Computer applications</topic><topic>Fluorescence</topic><topic>Fluorescent dyes</topic><topic>Fluorescent indicators</topic><topic>Fluorophores</topic><topic>Optical materials</topic><topic>Optics</topic><topic>Phosphoramidates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Machado, Luana A.</creatorcontrib><creatorcontrib>de Souza, Marcos C.</creatorcontrib><creatorcontrib>da Silva, Caroline M.</creatorcontrib><creatorcontrib>Yoneda, Julliane</creatorcontrib><creatorcontrib>de Rezende, Lucas C.D.</creatorcontrib><creatorcontrib>Emery, Flavio S.</creatorcontrib><creatorcontrib>de Simone, Carlos A.</creatorcontrib><creatorcontrib>da Silva Júnior, Eufrânio N.</creatorcontrib><creatorcontrib>Pedrosa, Leandro F.</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of fluorine chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Machado, Luana A.</au><au>de Souza, Marcos C.</au><au>da Silva, Caroline M.</au><au>Yoneda, Julliane</au><au>de Rezende, Lucas C.D.</au><au>Emery, Flavio S.</au><au>de Simone, Carlos A.</au><au>da Silva Júnior, Eufrânio N.</au><au>Pedrosa, Leandro F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>On the synthesis, optical and computational studies of novel BODIPY-based phosphoramidate fluorescent dyes</atitle><jtitle>Journal of fluorine chemistry</jtitle><date>2019-04</date><risdate>2019</risdate><volume>220</volume><spage>9</spage><epage>15</epage><pages>9-15</pages><issn>0022-1139</issn><eissn>1873-3328</eissn><abstract>New BODIPY fluorophores substituted with phosphoramidate groups have been synthesized and their photophysical properties were evaluated in details.
[Display omitted]
•Novel fluorescent probe based on the integration of aminoalkylphosphoramidate and BODIPY was designed.•Compounds were synthesized, well-characterized and their photophysical properties were investigated.•The BODIPY-based phosphoramidate derivatives containing fluorine are photostable with high absorption and emission in organic solvents.
New boro-dipyrromethene (BODIPY) fluorophores substituted with phosphoramidate groups have been synthesized using environmentally friendly methodologies, and their photophysical properties were evaluated experimentally and characterized in detail with respect to DFT and TD-DFT using B3LYP/6-31+G(d) level of theory. These fluorophores may be used as promising candidates for biological probes and optical materials.</abstract><cop>Lausanne</cop><pub>Elsevier B.V</pub><doi>10.1016/j.jfluchem.2019.01.008</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-2957-2307</orcidid><orcidid>https://orcid.org/0000-0003-2428-0396</orcidid></addata></record> |
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| identifier | ISSN: 0022-1139 |
| ispartof | Journal of fluorine chemistry, 2019-04, Vol.220, p.9-15 |
| issn | 0022-1139 1873-3328 |
| language | eng |
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| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | Biological materials BODIPY Chemical compounds Computational studies Computer applications Fluorescence Fluorescent dyes Fluorescent indicators Fluorophores Optical materials Optics Phosphoramidates |
| title | On the synthesis, optical and computational studies of novel BODIPY-based phosphoramidate fluorescent dyes |
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