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

Abstract

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

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1];  [1];  [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
  1. Department of Chemistry, Indiana University, Bloomington, USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1579762
Grant/Contract Number:  
FG02-09ER16068; SC0002728
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Organic and Biomolecular Chemistry
Additional Journal Information:
Journal Name: Organic and Biomolecular Chemistry; Journal ID: ISSN 1477-0520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

VanDenburgh, Katherine L., Liu, Yun, Sadhukhan, Tumpa, Benson, Christopher R., Cox, Natalie M., Erbas-Cakmak, Sundus, Qiao, Bo, Gao, Xinfeng, Pink, Maren, Raghavachari, Krishnan, and Flood, Amar H. Multi-state amine sensing by electron transfers in a BODIPY probe. United Kingdom: N. p., 2020. Web. doi:10.1039/C9OB02466B.
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. Multi-state amine sensing by electron transfers in a BODIPY probe. United Kingdom. doi:10.1039/C9OB02466B.
VanDenburgh, Katherine L., Liu, Yun, Sadhukhan, Tumpa, Benson, Christopher R., Cox, Natalie M., Erbas-Cakmak, Sundus, Qiao, Bo, Gao, Xinfeng, Pink, Maren, Raghavachari, Krishnan, and Flood, Amar H. Wed . "Multi-state amine sensing by electron transfers in a BODIPY probe". United Kingdom. doi:10.1039/C9OB02466B.
@article{osti_1579762,
title = {Multi-state amine sensing by electron transfers in a BODIPY probe},
author = {VanDenburgh, Katherine L. and Liu, Yun and Sadhukhan, Tumpa and Benson, Christopher R. and Cox, Natalie M. and Erbas-Cakmak, Sundus and Qiao, Bo and Gao, Xinfeng and Pink, Maren and Raghavachari, Krishnan and Flood, Amar H.},
abstractNote = {Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.},
doi = {10.1039/C9OB02466B},
journal = {Organic and Biomolecular Chemistry},
number = ,
volume = ,
place = {United Kingdom},
year = {2020},
month = {1}
}

Journal Article:
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This content will become publicly available on December 12, 2020
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Works referenced in this record:

Balance between Fluorescence Enhancement and Association Affinity in Fluorescent Heteroditopic Indicators for Imaging Zinc Ion in Living Cells
journal, October 2011

  • Kuang, Gui-Chao; Allen, John R.; Baird, Michelle A.
  • Inorganic Chemistry, Vol. 50, Issue 20
  • DOI: 10.1021/ic201728f

Highly effective discrimination of catecholamine derivatives via FRET-on/off processes induced by the intermolecular assembly with two fluorescence sensors
journal, January 2013

  • Chaicham, Anusak; Sahasithiwat, Somboon; Tuntulani, Thawatchai
  • Chemical Communications, Vol. 49, Issue 81
  • DOI: 10.1039/c3cc45077e

BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine
journal, November 2012

  • Niu, Li-Ya; Guan, Ying-Shi; Chen, Yu-Zhe
  • Journal of the American Chemical Society, Vol. 134, Issue 46
  • DOI: 10.1021/ja309079f

BODIPY Dyes and Their Derivatives:  Syntheses and Spectroscopic Properties
journal, November 2007

  • Loudet, Aurore; Burgess, Kevin
  • Chemical Reviews, Vol. 107, Issue 11
  • DOI: 10.1021/cr078381n

Proton and Electron Transfer in the Excited State Quenching of Phenosafranine by Aliphatic Amines†: Photochemistry and Photobiology, 2007, 83
journal, May 2007

  • Broglia, Martín F.; Bertolotti, Sonia G.; Previtali, Carlos M.
  • Photochemistry and Photobiology, Vol. 83, Issue 3
  • DOI: 10.1562/2006-07-31-RA-989

A BODIPY-based “OFF-ON” fluorescent probe for fast and selective detection of hypochlorite in living cells
journal, November 2019


Highly sensitive vapor detection of amines with fluorescent conjugated polymer: A novel lasing turn-on sensory mechanism
journal, April 2013


Turn on fluorescence sensing of vapor phase electron donating amines via tetraphenylporphyrin or metallophenylporphrin doped polyfluorene
journal, January 2010

  • He, Chao; He, Qingguo; Deng, Changmin
  • Chemical Communications, Vol. 46, Issue 40
  • DOI: 10.1039/c0cc01972k

A BODIPY dye as a reactive chromophoric/fluorogenic probe for selective and quick detection of vapors of secondary amines
journal, January 2013

  • Fu, Yanyan; He, Qingguo; Zhu, Defeng
  • Chemical Communications, Vol. 49, Issue 96
  • DOI: 10.1039/c3cc46571c

Fluorescent chemosensors: the past, present and future
journal, January 2017

  • Wu, Di; Sedgwick, Adam C.; Gunnlaugsson, Thorfinnur
  • Chemical Society Reviews, Vol. 46, Issue 23
  • DOI: 10.1039/C7CS00240H

Fluorescent signalling crown ethers; ‘switching on’ of fluorescence by alkali metal ion recognition and binding in situ
journal, January 1986

  • de Silva, A. Prasanna; de Silva, Saliya A.
  • J. Chem. Soc., Chem. Commun., Issue 23
  • DOI: 10.1039/C39860001709

Bimolecular photoinduced electron transfer between 7-methylbenzo[a]pyrene and aromatic amine donors in stationary and static regimes
journal, May 2019

  • Venkatesan, Munisamy; Mandal, Haraprasad; Bheerappagari, Ramakrishna
  • Journal of Photochemistry and Photobiology A: Chemistry, Vol. 376
  • DOI: 10.1016/j.jphotochem.2019.03.012

Quenching mechanism of quinolinium-type chloride-sensitive fluorescent indicators
journal, May 2000


Mini review: Fluorescent heteroditopic ligands of metal ions
journal, April 2009


Convenient and Efficient Synthesis of Functionalized Oligopyridine Ligands Bearing Accessory Pyrromethene-BF 2 Fluorophores
journal, March 2004

  • Ulrich, Gilles; Ziessel, Raymond
  • The Journal of Organic Chemistry, Vol. 69, Issue 6
  • DOI: 10.1021/jo035825g

Amine-responsive cellulose-based ratiometric fluorescent materials for real-time and visual detection of shrimp and crab freshness
journal, February 2019


Electron Transfer Triggers Fast Dimer/Monomer Switching of Pyridinium and Quinolinium Cations
journal, January 2012

  • Teplý, Filip; Čížková, Martina; Slavíček, Petr
  • The Journal of Physical Chemistry C, Vol. 116, Issue 5
  • DOI: 10.1021/jp211122n

The properties of organic liquids that are relevant to their use as solvating solvents
journal, January 1993


Determination of Enantiomeric Excess in Amine Derivatives with Molecular Self-Assemblies
journal, April 2015

  • Shcherbakova, Elena G.; Minami, Tsuyoshi; Brega, Valentina
  • Angewandte Chemie International Edition, Vol. 54, Issue 24
  • DOI: 10.1002/anie.201501736

Syntheses and Spectral Properties of Functionalized, Water-Soluble BODIPY Derivatives
journal, March 2008

  • Li, Lingling; Han, Junyan; Nguyen, Binh
  • The Journal of Organic Chemistry, Vol. 73, Issue 5
  • DOI: 10.1021/jo702463f

A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on the Distyryl−Bodipy Fluorophore
journal, September 2008

  • Atilgan, Serdar; Ozdemir, Tugba; Akkaya, Engin U.
  • Organic Letters, Vol. 10, Issue 18
  • DOI: 10.1021/ol801554t

Supercoiled fibres of self-sorted donor–acceptor stacks: a turn-off/turn-on platform for sensing volatile aromatic compounds
journal, January 2016

  • Sandeep, Anjamkudy; Praveen, Vakayil K.; Kartha, Kalathil K.
  • Chemical Science, Vol. 7, Issue 7
  • DOI: 10.1039/C6SC00629A

The triplet excited state of Bodipy: formation, modulation and application
journal, January 2015

  • Zhao, Jianzhang; Xu, Kejing; Yang, Wenbo
  • Chemical Society Reviews, Vol. 44, Issue 24
  • DOI: 10.1039/C5CS00364D

Detection of Amines with Fluorescent Nanotubes: Applications in the Assessment of Meat Spoilage
journal, October 2015


Destruction of azo dyes by anaerobic–aerobic sequential biological treatment: a review
journal, February 2014

  • Popli, S.; Patel, Upendra. D.
  • International Journal of Environmental Science and Technology, Vol. 12, Issue 1
  • DOI: 10.1007/s13762-014-0499-x

Photoinduced bimolecular electron transfer from aromatic amines to pentafluorophenyl porphyrin combined with ultrafast charge recombination persistence with Marcus inverted region
journal, January 2017

  • Venkatesh, Yeduru; Munisamy, Venkatesan; Ramakrishna, Bheerappagari
  • Physical Chemistry Chemical Physics, Vol. 19, Issue 7
  • DOI: 10.1039/C6CP08520B

“Turn-on” Fluorescence Sensing and Discriminative Detection of Aliphatic Amines Using a 5-Fold-Interpenetrated Coordination Polymer
journal, May 2017


Sacrificial electron donor reagents for solar fuel production
journal, March 2017


Rapid, specific, and ultrasensitive fluorogenic sensing of phosgene through an enhanced PeT mechanism
journal, March 2019


Photophysical Properties of Borondipyrromethene Analogues in Solution
journal, August 2005

  • Qin, Wenwu; Baruah, Mukulesh; Van der Auweraer, Mark
  • The Journal of Physical Chemistry A, Vol. 109, Issue 33
  • DOI: 10.1021/jp052626n

A Selective Fluorescent Sensor for Imaging Cd 2+ in Living Cells
journal, February 2007

  • Peng, Xiaojun; Du, Jianjun; Fan, Jiangli
  • Journal of the American Chemical Society, Vol. 129, Issue 6
  • DOI: 10.1021/ja0643319

Water-solubilisation and bio-conjugation of a red-emitting BODIPY marker
journal, January 2011

  • Niu, Song Lin; Massif, Cédrik; Ulrich, Gilles
  • Org. Biomol. Chem., Vol. 9, Issue 1
  • DOI: 10.1039/C0OB00693A

Noble-metal-free BODIPY–cobaloxime photocatalysts for visible-light-driven hydrogen production
journal, January 2014

  • Luo, Geng-Geng; Fang, Kai; Wu, Ji-Huai
  • Phys. Chem. Chem. Phys., Vol. 16, Issue 43
  • DOI: 10.1039/C4CP03343D

BODIPY Dye, the Most Versatile Fluorophore Ever?
journal, January 2016


A Highly Potassium-Selective Ratiometric Fluorescent Indicator Based on BODIPY Azacrown Ether Excitable with Visible Light
journal, September 2005

  • Baruah, Mukulesh; Qin, Wenwu; Vallée, Renaud A. L.
  • Organic Letters, Vol. 7, Issue 20
  • DOI: 10.1021/ol051603o

Electron Transfer from Aromatic Amines to Excited Coumarin Dyes:  Fluorescence Quenching and Picosecond Transient Absorption Studies
journal, January 2000

  • Nad, Sanjukta; Pal, Haridas
  • The Journal of Physical Chemistry A, Vol. 104, Issue 3
  • DOI: 10.1021/jp993206z

Primary and secondary amines in the human environment
journal, January 1977


Fluorescamine: A Reagent for Assay of Amino Acids, Peptides, Proteins, and Primary Amines in the Picomole Range
journal, November 1972


Water-Soluble BODIPY Derivatives
journal, May 2009

  • Niu, Song Lin; Ulrich, Gilles; Ziessel, Raymond
  • Organic Letters, Vol. 11, Issue 10
  • DOI: 10.1021/ol900302n

Design and Development of a New Pyrromethene Dye with Improved Photostability and Lasing Efficiency:  Theoretical Rationalization of Photophysical and Photochemical Properties
journal, March 2008

  • Mula, Soumyaditya; Ray, Alok K.; Banerjee, Manas
  • The Journal of Organic Chemistry, Vol. 73, Issue 6
  • DOI: 10.1021/jo702346s

Reaction-based BODIPY probes for selective bio-imaging
journal, January 2018


Biogenic amines in seafood: a review
journal, May 2016

  • Biji, K. B.; Ravishankar, C. N.; Venkateswarlu, R.
  • Journal of Food Science and Technology, Vol. 53, Issue 5
  • DOI: 10.1007/s13197-016-2224-x

A dual chromophore sensor for the detection of amines, diols, hydroxy acids, and amino alcohols
journal, January 2019

  • Pushina, Mariia; Farshbaf, Sepideh; Shcherbakova, Elena G.
  • Chemical Communications, Vol. 55, Issue 31
  • DOI: 10.1039/C9CC01051C

Current developments in fluorescent PET (photoinduced electron transfer) sensors and switches
journal, January 2015

  • Daly, Brian; Ling, Jue; de Silva, A. Prasanna
  • Chemical Society Reviews, Vol. 44, Issue 13
  • DOI: 10.1039/C4CS00334A

Bright, red emitting fluorescent sensor for intracellular imaging of Mg 2+
journal, January 2016

  • Lin, Qitian; Gruskos, Jessica J.; Buccella, Daniela
  • Organic & Biomolecular Chemistry, Vol. 14, Issue 48
  • DOI: 10.1039/C6OB02177H

Fluorene–thiophene-based thin-film fluorescent chemosensor for methamphetamine vapor by thiophene–amine interaction
journal, April 2013


A “turn-on-and-off” pH sensitive BODIPY fluorescent probe for imaging E. coli cells
journal, January 2018

  • Prasannan, Dijo; Arunkumar, Chellaiah
  • New Journal of Chemistry, Vol. 42, Issue 5
  • DOI: 10.1039/C7NJ04313A

A Heteroditopic Fluoroionophoric Platform for Constructing Fluorescent Probes with Large Dynamic Ranges for Zinc Ions
journal, March 2008

  • Zhang, Lu; Clark, Ronald J.; Zhu, Lei
  • Chemistry - A European Journal, Vol. 14, Issue 9
  • DOI: 10.1002/chem.200701419

New 8‐Amino‐BODIPY Derivatives: Surpassing Laser Dyes at Blue‐Edge Wavelengths
journal, May 2011

  • Bañuelos, Jorge; Martín, Virginia; Gómez‐Durán, C. F. Azael
  • Chemistry – A European Journal, Vol. 17, Issue 26
  • DOI: 10.1002/chem.201003689

Highly selective colorimetric and fluorescent BODIPY dyes for sensing of cysteine and/or homocysteine
journal, January 2016

  • Wu, Qinghua; Zhou, Jinyuan; Wu, Yangchun
  • New Journal of Chemistry, Vol. 40, Issue 2
  • DOI: 10.1039/C5NJ02346G

Electronic Excited State Redox Properties for BODIPY Dyes Predicted from Hammett Constants: Estimating the Driving Force of Photoinduced Electron Transfer
journal, August 2014

  • Lincoln, Richard; Greene, Lana E.; Krumova, Katerina
  • The Journal of Physical Chemistry A, Vol. 118, Issue 45
  • DOI: 10.1021/jp5059148

Reductive fluorescence quenching of DMP with aniline
journal, January 2014


Perylene derivatives as a fluorescent probe for sensing of amines in solution
journal, November 2016


Naphthalimide trifluoroacetyl acetonate: a hydrazine-selective chemodosimetric sensor
journal, January 2013

  • Lee, Min Hee; Yoon, Byungkwon; Kim, Jong Seung
  • Chemical Science, Vol. 4, Issue 11
  • DOI: 10.1039/c3sc51813b

Radioiodination of BODIPY and its application to a nuclear and optical dual functional labeling agent for proteins and peptides
journal, June 2017


Red‐Emitting Ratiometric Fluorescence Chemodosimeter for the Discriminative Detection of Aromatic and Aliphatic Amines
journal, July 2019

  • Sathiskumar, Udayadasan; Easwaramoorthi, Shanmugam
  • ChemistrySelect, Vol. 4, Issue 25
  • DOI: 10.1002/slct.201901254

Rapid Intersystem Crossing in Closely-Spaced but Orthogonal Molecular Dyads
journal, June 2007

  • Harriman, Anthony; Mallon, Laura J.; Ulrich, Gilles
  • ChemPhysChem, Vol. 8, Issue 8
  • DOI: 10.1002/cphc.200700060