Tetramethoxy-Aminorhodamine (TMARh): A Bichromophore, an Improved Fluorophore, and a pH Switch
Rhodamine is one of the most widely used fluorescent dyes. Here, a new synthetic pathway to the popular dyes is reported and the effect of adding four methoxy groups to the molecular structure is investigated. Tetramethoxy‐aminorhodamine (TMARh) is found to show superior pH switching compared to the...
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Veröffentlicht in: | Chemistry : a European journal 2016-05, Vol.22 (21), p.7046-7049 |
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creator | Sørensen, Thomas Just Shi, Dong Laursen, Bo W. |
description | Rhodamine is one of the most widely used fluorescent dyes. Here, a new synthetic pathway to the popular dyes is reported and the effect of adding four methoxy groups to the molecular structure is investigated. Tetramethoxy‐aminorhodamine (TMARh) is found to show superior pH switching compared to the rhodamine without the four methoxy groups, owing to changed properties of the dark “off” state and increased fluorescence intensity in the protonated “on” state.
A new route to rhodamines is reported, resulting in tetramethoxy‐rhodamines with improved photophysical properties. It was found that tetramethoxy‐aminorhodamine is a bichromophore and a very efficient pH‐responsive dye. |
doi_str_mv | 10.1002/chem.201600496 |
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A new route to rhodamines is reported, resulting in tetramethoxy‐rhodamines with improved photophysical properties. It was found that tetramethoxy‐aminorhodamine is a bichromophore and a very efficient pH‐responsive dye.</description><subject>Amination</subject><subject>bichromophores</subject><subject>Chemical compounds</subject><subject>Chemistry</subject><subject>Dyes</subject><subject>dyes/pigments</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Models, Molecular</subject><subject>Molecular structure</subject><subject>pH responsive dyes</subject><subject>photophysics</subject><subject>Protons</subject><subject>Rhodamine</subject><subject>Rhodamines - chemical synthesis</subject><subject>Rhodamines - chemistry</subject><subject>Spectrometry, Fluorescence</subject><subject>Switches</subject><subject>Switching</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1v00AQxVcIRNPClSOyxKWVcJjdtfeDWwhtUykFqQ0gcWC1sWdlFzsbdm3a_Pc4pATEpacZaX7vaWYeIS8ojCkAe1NU2I4ZUAGQafGIjGjOaMqlyB-TEehMpiLn-oAcxngDAFpw_pQcMKF1LoUYkW8L7IJtsav83SadtPXKh8qXdmgwOV5cTq6qk7fJJHlXF1XwrV9XPuDrxK6Si3Yd_E8sk7Om9-HvoExssp4l17d1V1TPyBNnm4jP7-sR-XR2upjO0vnH84vpZJ4WgkqRKpS0ZBlm2nIUnC05qiVKzgAKxbIMLONMOBQgCqedlJLlrnCOU5expVP8iBzvfIedfvQYO9PWscCmsSv0fTRUDR_KQEn9MCqVBq64ZAP66j_0xvdhNRyypRRQyH9T4x1VBB9jQGfWoW5t2BgKZhuS2YZk9iENgpf3tv2yxXKP_0llAPQOuK0b3DxgZ6az08t_zdOdto4d3u21Nnw3QnKZmy8fzg29Utfi_dfPZs5_AQRmqr8</recordid><startdate>20160517</startdate><enddate>20160517</enddate><creator>Sørensen, Thomas Just</creator><creator>Shi, Dong</creator><creator>Laursen, Bo W.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1120-3191</orcidid><orcidid>https://orcid.org/0000-0003-1491-5116</orcidid></search><sort><creationdate>20160517</creationdate><title>Tetramethoxy-Aminorhodamine (TMARh): A Bichromophore, an Improved Fluorophore, and a pH Switch</title><author>Sørensen, Thomas Just ; Shi, Dong ; Laursen, Bo W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6176-8e71d24e49a3e632b3e8be73200c82440a2326fe606cf9f77725fcff31f42bf83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Amination</topic><topic>bichromophores</topic><topic>Chemical compounds</topic><topic>Chemistry</topic><topic>Dyes</topic><topic>dyes/pigments</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Models, Molecular</topic><topic>Molecular structure</topic><topic>pH responsive dyes</topic><topic>photophysics</topic><topic>Protons</topic><topic>Rhodamine</topic><topic>Rhodamines - chemical synthesis</topic><topic>Rhodamines - chemistry</topic><topic>Spectrometry, Fluorescence</topic><topic>Switches</topic><topic>Switching</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sørensen, Thomas Just</creatorcontrib><creatorcontrib>Shi, Dong</creatorcontrib><creatorcontrib>Laursen, Bo W.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sørensen, Thomas Just</au><au>Shi, Dong</au><au>Laursen, Bo W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tetramethoxy-Aminorhodamine (TMARh): A Bichromophore, an Improved Fluorophore, and a pH Switch</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. 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subjects | Amination bichromophores Chemical compounds Chemistry Dyes dyes/pigments Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Hydrogen-Ion Concentration Models, Molecular Molecular structure pH responsive dyes photophysics Protons Rhodamine Rhodamines - chemical synthesis Rhodamines - chemistry Spectrometry, Fluorescence Switches Switching |
title | Tetramethoxy-Aminorhodamine (TMARh): A Bichromophore, an Improved Fluorophore, and a pH Switch |
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