Multi-state amine sensing by electron transfers in a BODIPY probe

Amines are ubiquitous in the chemical industry and are present in a wide range of biological processes, motivating the development of amine-sensitive sensors. There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by sing...

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Veröffentlicht in:Organic & biomolecular chemistry 2020-01, Vol.18 (3), p.431-44
Hauptverfasser: VanDenburgh, Katherine L, Liu, Yun, Sadhukhan, Tumpa, Benson, Christopher R, Cox, Natalie M, Erbas-Cakmak, Sundus, Qiao, Bo, Gao, Xinfeng, Pink, Maren, Raghavachari, Krishnan, Flood, Amar H
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container_issue 3
container_start_page 431
container_title Organic & biomolecular chemistry
container_volume 18
creator VanDenburgh, Katherine L
Liu, Yun
Sadhukhan, Tumpa
Benson, Christopher R
Cox, Natalie M
Erbas-Cakmak, Sundus
Qiao, Bo
Gao, Xinfeng
Pink, Maren
Raghavachari, Krishnan
Flood, Amar H
description Amines are ubiquitous in the chemical industry and are present in a wide range of biological processes, motivating the development of amine-sensitive sensors. There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by single electron transfer (SET). We investigated a new turn-on amine probe with a 4,4-difluoro-4-bora-3a,4a-diaza- s -indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor. Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.
doi_str_mv 10.1039/c9ob02466b
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There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by single electron transfer (SET). We investigated a new turn-on amine probe with a 4,4-difluoro-4-bora-3a,4a-diaza- s -indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor. 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Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.</description><subject>Alcohols</subject><subject>Aliphatic amines</subject><subject>Amines</subject><subject>Amines - analysis</subject><subject>Biological activity</subject><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - chemistry</subject><subject>Charge transfer</subject><subject>Chemical industry</subject><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Density Functional Theory</subject><subject>Electron transfer</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Low concentrations</subject><subject>Models, Chemical</subject><subject>Organic chemistry</subject><subject>Physical Sciences</subject><subject>Quenching</subject><subject>Quinolinium Compounds - chemical synthesis</subject><subject>Quinolinium Compounds - chemistry</subject><subject>Science &amp; 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Liu, Yun ; Sadhukhan, Tumpa ; Benson, Christopher R ; Cox, Natalie M ; Erbas-Cakmak, Sundus ; Qiao, Bo ; Gao, Xinfeng ; Pink, Maren ; Raghavachari, Krishnan ; Flood, Amar H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c466t-375b1b771009ac6451c1e096363f4cedadd75918cd723c18d51565a9eae948013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alcohols</topic><topic>Aliphatic amines</topic><topic>Amines</topic><topic>Amines - analysis</topic><topic>Biological activity</topic><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - chemistry</topic><topic>Charge transfer</topic><topic>Chemical industry</topic><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Density Functional Theory</topic><topic>Electron transfer</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Low concentrations</topic><topic>Models, Chemical</topic><topic>Organic chemistry</topic><topic>Physical Sciences</topic><topic>Quenching</topic><topic>Quinolinium Compounds - chemical synthesis</topic><topic>Quinolinium Compounds - chemistry</topic><topic>Science &amp; Technology</topic><topic>Sensors</topic><topic>Shutdowns</topic><topic>Single electrons</topic><topic>Spectrometry, Fluorescence - methods</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>VanDenburgh, Katherine L</creatorcontrib><creatorcontrib>Liu, Yun</creatorcontrib><creatorcontrib>Sadhukhan, Tumpa</creatorcontrib><creatorcontrib>Benson, Christopher R</creatorcontrib><creatorcontrib>Cox, Natalie M</creatorcontrib><creatorcontrib>Erbas-Cakmak, Sundus</creatorcontrib><creatorcontrib>Qiao, Bo</creatorcontrib><creatorcontrib>Gao, Xinfeng</creatorcontrib><creatorcontrib>Pink, Maren</creatorcontrib><creatorcontrib>Raghavachari, Krishnan</creatorcontrib><creatorcontrib>Flood, Amar H</creatorcontrib><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>OSTI.GOV</collection><jtitle>Organic &amp; 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There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by single electron transfer (SET). We investigated a new turn-on amine probe with a 4,4-difluoro-4-bora-3a,4a-diaza- s -indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor. 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subjects Alcohols
Aliphatic amines
Amines
Amines - analysis
Biological activity
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Charge transfer
Chemical industry
Chemistry
Chemistry, Organic
Crystal structure
Crystallography
Density Functional Theory
Electron transfer
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Low concentrations
Models, Chemical
Organic chemistry
Physical Sciences
Quenching
Quinolinium Compounds - chemical synthesis
Quinolinium Compounds - chemistry
Science & Technology
Sensors
Shutdowns
Single electrons
Spectrometry, Fluorescence - methods
Thiols
title Multi-state amine sensing by electron transfers in a BODIPY probe
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