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

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.

doi:10.1039/C9OB02466B

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

Journal Article · 11 December 2019 · Organic and Biomolecular Chemistry

DOI: https://doi.org/10.1039/C9OB02466B · OSTI ID:1608106

^[1];

^[2];

^[2]; Benson, Christopher R. ^[2]; Cox, Natalie M. ^[2];

^[2];

^[2]

Indiana Univ., Bloomington, IN (United States); Indiana University
Indiana Univ., Bloomington, IN (United States)

Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Indiana Univ., Bloomington, IN (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: SC0002728

OSTI ID:: 1608106

Journal Information:: Organic and Biomolecular Chemistry, Journal Name: Organic and Biomolecular Chemistry Journal Issue: 3 Vol. 18; ISSN OBCRAK; ISSN 1477-0520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (63)

Determination of Enantiomeric Excess in Amine Derivatives with Molecular Self-Assemblies Shcherbakova, Elena G.; Minami, Tsuyoshi; Brega, Valentina Angewandte Chemie, Vol. 127, Issue 24 https://doi.org/10.1002/ange.201501736	journal	April 2015
Determination of Enantiomeric Excess in Amine Derivatives with Molecular Self-Assemblies Shcherbakova, Elena G.; Minami, Tsuyoshi; Brega, Valentina Angewandte Chemie International Edition, Vol. 54, Issue 24 https://doi.org/10.1002/anie.201501736	journal	April 2015
A Heteroditopic Fluoroionophoric Platform for Constructing Fluorescent Probes with Large Dynamic Ranges for Zinc Ions Zhang, Lu; Clark, Ronald J.; Zhu, Lei Chemistry - A European Journal, Vol. 14, Issue 9 https://doi.org/10.1002/chem.200701419	journal	March 2008
New 8‐Amino‐BODIPY Derivatives: Surpassing Laser Dyes at Blue‐Edge Wavelengths Bañuelos, Jorge; Martín, Virginia; Gómez‐Durán, C. F. Azael Chemistry – A European Journal, Vol. 17, Issue 26 https://doi.org/10.1002/chem.201003689	journal	May 2011
Rapid Intersystem Crossing in Closely-Spaced but Orthogonal Molecular Dyads Harriman, Anthony; Mallon, Laura J.; Ulrich, Gilles ChemPhysChem, Vol. 8, Issue 8 https://doi.org/10.1002/cphc.200700060	journal	June 2007
Spirofluorene-Cored Difluoroboron β-Diketonate Complexes with Terminal Carbazole: Synthesis, Self-Assembling, and Fluorescent Sensory Properties: Spirofluorene-Cored Difluoroboron β-Diketonate Complexes with Terminal Carbazole: Synthesis, Self-Assembling, and Fluorescent Sensory Properties Zhai, Lu; Shu, Yuanhong; Sun, Jingbo European Journal of Organic Chemistry, Vol. 2019, Issue 20 https://doi.org/10.1002/ejoc.201900161	journal	May 2019
Red‐Emitting Ratiometric Fluorescence Chemodosimeter for the Discriminative Detection of Aromatic and Aliphatic Amines Sathiskumar, Udayadasan; Easwaramoorthi, Shanmugam ChemistrySelect, Vol. 4, Issue 25 https://doi.org/10.1002/slct.201901254	journal	July 2019
BODIPY Dye, the Most Versatile Fluorophore Ever? Bañuelos, Jorge The Chemical Record, Vol. 16, Issue 1 https://doi.org/10.1002/tcr.201500238	journal	January 2016
Biogenic amines in seafood: a review Biji, K. B.; Ravishankar, C. N.; Venkateswarlu, R. Journal of Food Science and Technology, Vol. 53, Issue 5 https://doi.org/10.1007/s13197-016-2224-x	journal	May 2016
Destruction of azo dyes by anaerobic–aerobic sequential biological treatment: a review Popli, S.; Patel, Upendra. D. International Journal of Environmental Science and Technology, Vol. 12, Issue 1 https://doi.org/10.1007/s13762-014-0499-x	journal	February 2014
Tetrathylammonium contains an impurity which alkalizes cytoplasm and reduce calcium buffering in neurons Zucker, Robert S. Brain Research, Vol. 208, Issue 2 https://doi.org/10.1016/0006-8993(81)90580-1	journal	March 1981
Biological significance of trace levels of mutagenic heterocyclic aromatic amines in human diet: A critical review Stavric, B. Food and Chemical Toxicology, Vol. 32, Issue 10 https://doi.org/10.1016/0278-6915(94)90093-0	journal	October 1994
Primary and secondary amines in the human environment Neurath, G. B.; Dünger, M.; Pein, F. G. Food and Cosmetics Toxicology, Vol. 15, Issue 4 https://doi.org/10.1016/S0015-6264(77)80197-1	journal	January 1977
Quenching mechanism of quinolinium-type chloride-sensitive fluorescent indicators Jayaraman, Sujatha; Verkman, A. S. Biophysical Chemistry, Vol. 85, Issue 1 https://doi.org/10.1016/S0301-4622(00)00146-0	journal	May 2000
Reaction-based BODIPY probes for selective bio-imaging Kolemen, Safacan; Akkaya, Engin U. Coordination Chemistry Reviews, Vol. 354 https://doi.org/10.1016/j.ccr.2017.06.021	journal	January 2018
Sacrificial electron donor reagents for solar fuel production Pellegrin, Yann; Odobel, Fabrice Comptes Rendus Chimie, Vol. 20, Issue 3 https://doi.org/10.1016/j.crci.2015.11.026	journal	March 2017
Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters Pinheiro, H. M.; Touraud, E.; Thomas, O. Dyes and Pigments, Vol. 61, Issue 2 https://doi.org/10.1016/j.dyepig.2003.10.009	journal	May 2004
Perylene derivatives as a fluorescent probe for sensing of amines in solution Sriramulu, Deepa; Valiyaveettil, Suresh Dyes and Pigments, Vol. 134 https://doi.org/10.1016/j.dyepig.2016.07.028	journal	November 2016
A BODIPY-based “OFF-ON” fluorescent probe for fast and selective detection of hypochlorite in living cells Shi, Wen-Jing; Huang, Yan; Liu, Wancui Dyes and Pigments, Vol. 170 https://doi.org/10.1016/j.dyepig.2019.107566	journal	November 2019
Reductive fluorescence quenching of DMP with aniline Asha Jhonsi, M.; Kathiravan, A. Journal of Luminescence, Vol. 145 https://doi.org/10.1016/j.jlumin.2013.07.017	journal	January 2014
Bimolecular photoinduced electron transfer between 7-methylbenzo[a]pyrene and aromatic amine donors in stationary and static regimes Venkatesan, Munisamy; Mandal, Haraprasad; Bheerappagari, Ramakrishna Journal of Photochemistry and Photobiology A: Chemistry, Vol. 376 https://doi.org/10.1016/j.jphotochem.2019.03.012	journal	May 2019
Fluorene–thiophene-based thin-film fluorescent chemosensor for methamphetamine vapor by thiophene–amine interaction Fu, Yanyan; Shi, Liqi; Zhu, Defeng Sensors and Actuators B: Chemical, Vol. 180 https://doi.org/10.1016/j.snb.2011.10.031	journal	April 2013
Highly sensitive vapor detection of amines with fluorescent conjugated polymer: A novel lasing turn-on sensory mechanism Dong, Lin; Deng, Changmin; He, Chao Sensors and Actuators B: Chemical, Vol. 180 https://doi.org/10.1016/j.snb.2011.11.046	journal	April 2013
Rapid, specific, and ultrasensitive fluorogenic sensing of phosgene through an enhanced PeT mechanism Kim, Tae-Il; Kim, Dami; Bouffard, Jean Sensors and Actuators B: Chemical, Vol. 283 https://doi.org/10.1016/j.snb.2018.12.017	journal	March 2019
“Turn-on” Fluorescence Sensing and Discriminative Detection of Aliphatic Amines Using a 5-Fold-Interpenetrated Coordination Polymer Mani, Prabu; Ojha, Anupam Anand; Reddy, Vennapusa Sivaranjana Inorganic Chemistry, Vol. 56, Issue 12 https://doi.org/10.1021/acs.inorgchem.7b00787	journal	May 2017
Detection of Amines with Fluorescent Nanotubes: Applications in the Assessment of Meat Spoilage Hu, Yanyong; Ma, Xiaojie; Zhang, Yibin ACS Sensors, Vol. 1, Issue 1 https://doi.org/10.1021/acssensors.5b00040	journal	October 2015
BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties Loudet, Aurore; Burgess, Kevin Chemical Reviews, Vol. 107, Issue 11 https://doi.org/10.1021/cr078381n	journal	November 2007
Balance between Fluorescence Enhancement and Association Affinity in Fluorescent Heteroditopic Indicators for Imaging Zinc Ion in Living Cells Kuang, Gui-Chao; Allen, John R.; Baird, Michelle A. Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic201728f	journal	October 2011
A Selective Fluorescent Sensor for Imaging Cd ²⁺ in Living Cells Peng, Xiaojun; Du, Jianjun; Fan, Jiangli Journal of the American Chemical Society, Vol. 129, Issue 6 https://doi.org/10.1021/ja0643319	journal	February 2007
BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine Niu, Li-Ya; Guan, Ying-Shi; Chen, Yu-Zhe Journal of the American Chemical Society, Vol. 134, Issue 46 https://doi.org/10.1021/ja309079f	journal	November 2012
Convenient and Efficient Synthesis of Functionalized Oligopyridine Ligands Bearing Accessory Pyrromethene-BF ₂ Fluorophores Ulrich, Gilles; Ziessel, Raymond The Journal of Organic Chemistry, Vol. 69, Issue 6 https://doi.org/10.1021/jo035825g	journal	March 2004
Design and Development of a New Pyrromethene Dye with Improved Photostability and Lasing Efficiency: Theoretical Rationalization of Photophysical and Photochemical Properties Mula, Soumyaditya; Ray, Alok K.; Banerjee, Manas The Journal of Organic Chemistry, Vol. 73, Issue 6 https://doi.org/10.1021/jo702346s	journal	March 2008
Syntheses and Spectral Properties of Functionalized, Water-Soluble BODIPY Derivatives Li, Lingling; Han, Junyan; Nguyen, Binh The Journal of Organic Chemistry, Vol. 73, Issue 5 https://doi.org/10.1021/jo702463f	journal	March 2008
Photophysical Properties of Borondipyrromethene Analogues in Solution Qin, Wenwu; Baruah, Mukulesh; Van der Auweraer, Mark The Journal of Physical Chemistry A, Vol. 109, Issue 33 https://doi.org/10.1021/jp052626n	journal	August 2005
Electron Transfer Triggers Fast Dimer/Monomer Switching of Pyridinium and Quinolinium Cations Teplý, Filip; Čížková, Martina; Slavíček, Petr The Journal of Physical Chemistry C, Vol. 116, Issue 5 https://doi.org/10.1021/jp211122n	journal	January 2012
Electronic Excited State Redox Properties for BODIPY Dyes Predicted from Hammett Constants: Estimating the Driving Force of Photoinduced Electron Transfer Lincoln, Richard; Greene, Lana E.; Krumova, Katerina The Journal of Physical Chemistry A, Vol. 118, Issue 45 https://doi.org/10.1021/jp5059148	journal	August 2014
Electron Transfer from Aromatic Amines to Excited Coumarin Dyes: Fluorescence Quenching and Picosecond Transient Absorption Studies Nad, Sanjukta; Pal, Haridas The Journal of Physical Chemistry A, Vol. 104, Issue 3 https://doi.org/10.1021/jp993206z	journal	January 2000
A Highly Potassium-Selective Ratiometric Fluorescent Indicator Based on BODIPY Azacrown Ether Excitable with Visible Light Baruah, Mukulesh; Qin, Wenwu; Vallée, Renaud A. L. Organic Letters, Vol. 7, Issue 20 https://doi.org/10.1021/ol051603o	journal	September 2005
A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on the Distyryl−Bodipy Fluorophore Atilgan, Serdar; Ozdemir, Tugba; Akkaya, Engin U. Organic Letters, Vol. 10, Issue 18 https://doi.org/10.1021/ol801554t	journal	September 2008
Water-Soluble BODIPY Derivatives Niu, Song Lin; Ulrich, Gilles; Ziessel, Raymond Organic Letters, Vol. 11, Issue 10 https://doi.org/10.1021/ol900302n	journal	May 2009
Amine-responsive cellulose-based ratiometric fluorescent materials for real-time and visual detection of shrimp and crab freshness Jia, Ruonan; Tian, Weiguo; Bai, Haotian Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-08675-3	journal	February 2019
Radioiodination of BODIPY and its application to a nuclear and optical dual functional labeling agent for proteins and peptides Ono, Masahiro; Watanabe, Hiroyuki; Ikehata, Yuki Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/s41598-017-03419-z	journal	June 2017
Water-solubilisation and bio-conjugation of a red-emitting BODIPY marker Niu, Song Lin; Massif, Cédrik; Ulrich, Gilles Org. Biomol. Chem., Vol. 9, Issue 1 https://doi.org/10.1039/C0OB00693A	journal	January 2011
Fluorescent signalling crown ethers; ‘switching on’ of fluorescence by alkali metal ion recognition and binding in situ de Silva, A. Prasanna; de Silva, Saliya A. J. Chem. Soc., Chem. Commun., Issue 23 https://doi.org/10.1039/C39860001709	journal	January 1986
Noble-metal-free BODIPY–cobaloxime photocatalysts for visible-light-driven hydrogen production Luo, Geng-Geng; Fang, Kai; Wu, Ji-Huai Phys. Chem. Chem. Phys., Vol. 16, Issue 43 https://doi.org/10.1039/C4CP03343D	journal	January 2014
Current developments in fluorescent PET (photoinduced electron transfer) sensors and switches Daly, Brian; Ling, Jue; de Silva, A. Prasanna Chemical Society Reviews, Vol. 44, Issue 13 https://doi.org/10.1039/C4CS00334A	journal	January 2015
The triplet excited state of Bodipy: formation, modulation and application Zhao, Jianzhang; Xu, Kejing; Yang, Wenbo Chemical Society Reviews, Vol. 44, Issue 24 https://doi.org/10.1039/C5CS00364D	journal	January 2015
Highly selective colorimetric and fluorescent BODIPY dyes for sensing of cysteine and/or homocysteine Wu, Qinghua; Zhou, Jinyuan; Wu, Yangchun New Journal of Chemistry, Vol. 40, Issue 2 https://doi.org/10.1039/C5NJ02346G	journal	January 2016
Photoinduced bimolecular electron transfer from aromatic amines to pentafluorophenyl porphyrin combined with ultrafast charge recombination persistence with Marcus inverted region Venkatesh, Yeduru; Munisamy, Venkatesan; Ramakrishna, Bheerappagari Physical Chemistry Chemical Physics, Vol. 19, Issue 7 https://doi.org/10.1039/C6CP08520B	journal	January 2017
Bright, red emitting fluorescent sensor for intracellular imaging of Mg ²⁺ Lin, Qitian; Gruskos, Jessica J.; Buccella, Daniela Organic & Biomolecular Chemistry, Vol. 14, Issue 48 https://doi.org/10.1039/C6OB02177H	journal	January 2016
Supercoiled fibres of self-sorted donor–acceptor stacks: a turn-off/turn-on platform for sensing volatile aromatic compounds Sandeep, Anjamkudy; Praveen, Vakayil K.; Kartha, Kalathil K. Chemical Science, Vol. 7, Issue 7 https://doi.org/10.1039/C6SC00629A	journal	January 2016
Fluorescent chemosensors: the past, present and future Wu, Di; Sedgwick, Adam C.; Gunnlaugsson, Thorfinnur Chemical Society Reviews, Vol. 46, Issue 23 https://doi.org/10.1039/C7CS00240H	journal	January 2017
A “turn-on-and-off” pH sensitive BODIPY fluorescent probe for imaging E. coli cells Prasannan, Dijo; Arunkumar, Chellaiah New Journal of Chemistry, Vol. 42, Issue 5 https://doi.org/10.1039/C7NJ04313A	journal	January 2018
A dual chromophore sensor for the detection of amines, diols, hydroxy acids, and amino alcohols Pushina, Mariia; Farshbaf, Sepideh; Shcherbakova, Elena G. Chemical Communications, Vol. 55, Issue 31 https://doi.org/10.1039/C9CC01051C	journal	January 2019
Turn on fluorescence sensing of vapor phase electron donating amines via tetraphenylporphyrin or metallophenylporphrin doped polyfluorene He, Chao; He, Qingguo; Deng, Changmin Chemical Communications, Vol. 46, Issue 40 https://doi.org/10.1039/c0cc01972k	journal	January 2010
Highly effective discrimination of catecholamine derivatives via FRET-on/off processes induced by the intermolecular assembly with two fluorescence sensors Chaicham, Anusak; Sahasithiwat, Somboon; Tuntulani, Thawatchai Chemical Communications, Vol. 49, Issue 81 https://doi.org/10.1039/c3cc45077e	journal	January 2013
A BODIPY dye as a reactive chromophoric/fluorogenic probe for selective and quick detection of vapors of secondary amines Fu, Yanyan; He, Qingguo; Zhu, Defeng Chemical Communications, Vol. 49, Issue 96 https://doi.org/10.1039/c3cc46571c	journal	January 2013
Iodo-Bodipys as visible-light-absorbing dual-functional photoredox catalysts for preparation of highly functionalized organic compounds by formation of C–C bonds via reductive and oxidative quenching catalytic mechanisms Huang, Ling; Zhao, Jianzhang RSC Advances, Vol. 3, Issue 45 https://doi.org/10.1039/c3ra43299h	journal	January 2013
Naphthalimide trifluoroacetyl acetonate: a hydrazine-selective chemodosimetric sensor Lee, Min Hee; Yoon, Byungkwon; Kim, Jong Seung Chemical Science, Vol. 4, Issue 11 https://doi.org/10.1039/c3sc51813b	journal	January 2013
The properties of organic liquids that are relevant to their use as solvating solvents Marcus, Y. Chemical Society Reviews, Vol. 22, Issue 6 https://doi.org/10.1039/cs9932200409	journal	January 1993
Mini review: Fluorescent heteroditopic ligands of metal ions Zhu, Lei; Zhang, Lu; Younes, Ali H. Supramolecular Chemistry, Vol. 21, Issue 3-4 https://doi.org/10.1080/10610270802538298	journal	April 2009
Fluorescamine: A Reagent for Assay of Amino Acids, Peptides, Proteins, and Primary Amines in the Picomole Range Udenfriend, S.; Stein, S.; Bohlen, P. Science, Vol. 178, Issue 4063 https://doi.org/10.1126/science.178.4063.871	journal	November 1972
Proton and Electron Transfer in the Excited State Quenching of Phenosafranine by Aliphatic Amines†: Photochemistry and Photobiology, 2007, 83 Broglia, Martín F.; Bertolotti, Sonia G.; Previtali, Carlos M. Photochemistry and Photobiology, Vol. 83, Issue 3 https://doi.org/10.1562/2006-07-31-RA-989	journal	May 2007

Similar Records

Experimental investigation of excited-state electron-transfer reaction: Effects of free energy and solvent on rates

Journal Article · 1990 · Journal of Physical Chemistry; (USA) · OSTI ID:6547358

Chen, Jingming; Ho, Tonging; Mou, Chungyuan

A Photoactivatable BODIPY Probe for Localization-based Super-Resolution Cellular Imaging

Journal Article · 2018 · Angewandte Chemie (International Edition) · OSTI ID:1464487

Wijesooriya, Chamari S.; Peterson, Julie A.; Shrestha, Pradeep; +3 more

A Photoactivatable BODIPY Probe for Localization‐Based Super‐Resolution Cellular Imaging

Journal Article · 2018 · Angewandte Chemie · OSTI ID:1468372

Wijesooriya, Chamari S.; Peterson, Julie A.; Shrestha, Pradeep; +3 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

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

Citation Formats

References (63)

Linked Research (1)

Similar Records

Related Subjects