skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: New molecular design for blue BODIPYs

Abstract

Dihydro analogues of BODIPYs exhibit spectral features ( Φ f ∼ 0.4–0.9) resembling aminocoumarins and suggest applications for broad-band photosensitization or where large Stokes shifts are desired.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [4]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [1]
  1. Department of Chemistry, North Carolina State University, Raleigh, USA
  2. Department of Chemistry, Washington University, St. Louis, USA
  3. Department of Chemistry, University of California, Riverside, USA
  4. Department of Energy, Environmental & Chemical Engineering, and Center for Solar Energy and Energy Storage, Washington University, St. Louis, USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1508412
Grant/Contract Number:  
FG02-05ER15661
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
New Journal of Chemistry
Additional Journal Information:
Journal Name: New Journal of Chemistry Journal Volume: 43 Journal Issue: 19; Journal ID: ISSN 1144-0546
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Wu, Zhiyuan, Fujita, Hikaru, Magdaong, Nikki Cecil M., Diers, James R., Hood, Don, Allu, Srinivasarao, Niedzwiedzki, Dariusz M., Kirmaier, Christine, Bocian, David F., Holten, Dewey, and Lindsey, Jonathan S. New molecular design for blue BODIPYs. United Kingdom: N. p., 2019. Web. doi:10.1039/C9NJ01114E.
Wu, Zhiyuan, Fujita, Hikaru, Magdaong, Nikki Cecil M., Diers, James R., Hood, Don, Allu, Srinivasarao, Niedzwiedzki, Dariusz M., Kirmaier, Christine, Bocian, David F., Holten, Dewey, & Lindsey, Jonathan S. New molecular design for blue BODIPYs. United Kingdom. doi:10.1039/C9NJ01114E.
Wu, Zhiyuan, Fujita, Hikaru, Magdaong, Nikki Cecil M., Diers, James R., Hood, Don, Allu, Srinivasarao, Niedzwiedzki, Dariusz M., Kirmaier, Christine, Bocian, David F., Holten, Dewey, and Lindsey, Jonathan S. Tue . "New molecular design for blue BODIPYs". United Kingdom. doi:10.1039/C9NJ01114E.
@article{osti_1508412,
title = {New molecular design for blue BODIPYs},
author = {Wu, Zhiyuan and Fujita, Hikaru and Magdaong, Nikki Cecil M. and Diers, James R. and Hood, Don and Allu, Srinivasarao and Niedzwiedzki, Dariusz M. and Kirmaier, Christine and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.},
abstractNote = {Dihydro analogues of BODIPYs exhibit spectral features ( Φ f ∼ 0.4–0.9) resembling aminocoumarins and suggest applications for broad-band photosensitization or where large Stokes shifts are desired.},
doi = {10.1039/C9NJ01114E},
journal = {New Journal of Chemistry},
number = 19,
volume = 43,
place = {United Kingdom},
year = {2019},
month = {5}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C9NJ01114E

Citation Metrics:
Cited by: 1 work
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

BODIPY-based probes for the fluorescence imaging of biomolecules in living cells
journal, January 2015

  • Kowada, Toshiyuki; Maeda, Hiroki; Kikuchi, Kazuya
  • Chemical Society Reviews, Vol. 44, Issue 14
  • DOI: 10.1039/C5CS00030K

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

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


Hydroboration of isoprene and 1,4-cyclooctadiene with N-azolylboranes
journal, April 1997


Design, Synthesis, and Photodynamics of Light-Harvesting Arrays Comprised of a Porphyrin and One, Two, or Eight Boron-Dipyrrin Accessory Pigments
journal, October 1998

  • Li, Feirong; Yang, Sung Ik; Ciringh, Yangzhen
  • Journal of the American Chemical Society, Vol. 120, Issue 39
  • DOI: 10.1021/ja9812047

Annulated bacteriochlorins for near-infrared photophysical studies
journal, January 2019

  • Fujita, Hikaru; Jing, Haoyu; Krayer, Michael
  • New Journal of Chemistry, Vol. 43, Issue 19
  • DOI: 10.1039/c9nj01113g

Unusual Photophysical Properties of Coumarin-151
journal, February 2001

  • Nad, Sanjukta; Pal, Haridas
  • The Journal of Physical Chemistry A, Vol. 105, Issue 7
  • DOI: 10.1021/jp003157m

Database of Absorption and Fluorescence Spectra of >300 Common Compounds for use in PhotochemCAD
journal, February 2018

  • Taniguchi, Masahiko; Lindsey, Jonathan S.
  • Photochemistry and Photobiology, Vol. 94, Issue 2
  • DOI: 10.1111/php.12860

8-Amino-BODIPYs: Structural Variation, Solvent-Dependent Emission, and VT NMR Spectroscopic Properties of 8-R 2 N-BODIPY
journal, April 2013

  • Roacho, Robinson I.; Metta-Magaña, Alejandro; Portillo, Michelle M.
  • The Journal of Organic Chemistry, Vol. 78, Issue 9
  • DOI: 10.1021/jo302758a

Lewis Acid-Promoted Oxidative Addition of Thioimidates to Pd(0)
journal, December 2002

  • Ghosh, Indranath; Jacobi, Peter A.
  • The Journal of Organic Chemistry, Vol. 67, Issue 26
  • DOI: 10.1021/jo026510o

Boron-Complexation Strategy for Use with 1-Acyldipyrromethanes
journal, August 2004

  • Muthukumaran, Kannan; Ptaszek, Marcin; Noll, Bruce
  • The Journal of Organic Chemistry, Vol. 69, Issue 16
  • DOI: 10.1021/jo0492620

Molecular Origins of Optoelectronic Properties in Coumarin Dyes: Toward Designer Solar Cell and Laser Applications
journal, December 2011

  • Liu, Xiaogang; Cole, Jacqueline M.; Waddell, Paul G.
  • The Journal of Physical Chemistry A, Vol. 116, Issue 1
  • DOI: 10.1021/jp209925y

Synthesis and photophysical characterization of bacteriochlorins equipped with integral swallowtail substituents
journal, January 2017

  • Liu, Yizhou; Allu, Srinivasarao; Nagarjuna Reddy, Muthyala
  • New Journal of Chemistry, Vol. 41, Issue 11
  • DOI: 10.1039/C7NJ00499K

New heteroaromatic compounds. XXV. Studies of salt formation in boron oxyacids by boron-11 nuclear magnetic resonance
journal, May 1967

  • Dewar, Michael J. S.; Jones, Richard.
  • Journal of the American Chemical Society, Vol. 89, Issue 10
  • DOI: 10.1021/ja00986a029

Substituent and Solvent Effects on the Nature of the Transitions of Pyrenol and Pyranine. Identification of an Intermediate in the Excited-State Proton-Transfer Reaction
journal, March 2002

  • Tran-Thi, T. -H.; Prayer, C.; Millié, Ph.
  • The Journal of Physical Chemistry A, Vol. 106, Issue 10
  • DOI: 10.1021/jp0125606

Difluorboryl-Komplexe von Di- und Tripyrrylmethenen
journal, December 1968

  • Treibs, Alfred; Kreuzer, Franz-Heinrich
  • Justus Liebigs Annalen der Chemie, Vol. 718, Issue 1
  • DOI: 10.1002/jlac.19687180119

Hydrogen Bonding Properties of Coumarin 151, 500, and 35:  The Effect of Substitution at the 7-Amino Position
journal, February 2006

  • Das, K.; Jain, B.; Patel, H. S.
  • The Journal of Physical Chemistry A, Vol. 110, Issue 5
  • DOI: 10.1021/jp0556411

Regioselective β-pyrrolic electrophilic substitution of hydrodipyrrin–dialkylboron complexes facilitates access to synthetic models for chlorophyll f
journal, January 2014

  • Liu, Mengran; Ptaszek, Marcin; Mass, Olga
  • New Journal of Chemistry, Vol. 38, Issue 4
  • DOI: 10.1039/c3nj01508d

Northern–Southern Route to Synthetic Bacteriochlorins
journal, November 2016

  • Liu, Yizhou; Lindsey, Jonathan S.
  • The Journal of Organic Chemistry, Vol. 81, Issue 23
  • DOI: 10.1021/acs.joc.6b02334

Boron dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy
journal, January 2012


Far-red and near infrared BODIPY dyes: synthesis and applications for fluorescent pH probes and bio-imaging
journal, January 2014

  • Ni, Yong; Wu, Jishan
  • Organic & Biomolecular Chemistry, Vol. 12, Issue 23
  • DOI: 10.1039/c3ob42554a

Synthesis of tailored hydrodipyrrins and their examination in directed routes to bacteriochlorins and tetradehydrocorrins
journal, January 2017

  • Zhang, Shaofei; Nagarjuna Reddy, Muthyala; Mass, Olga
  • New Journal of Chemistry, Vol. 41, Issue 19
  • DOI: 10.1039/C7NJ01892D

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

Boron-dipyrromethene dyes for incorporation in synthetic multi-pigment light-harvesting arrays
journal, January 1996


Lighting the way ahead with boron dipyrromethene (Bodipy) dyes
journal, January 2009

  • Benniston, Andrew C.; Copley, Graeme
  • Physical Chemistry Chemical Physics, Vol. 11, Issue 21
  • DOI: 10.1039/b901383k

Fluorescent indicators based on BODIPY
journal, January 2012

  • Boens, Noël; Leen, Volker; Dehaen, Wim
  • Chem. Soc. Rev., Vol. 41, Issue 3
  • DOI: 10.1039/C1CS15132K

The chemistry of Bodipy: A new El Dorado for fluorescence tools
journal, January 2007

  • Ziessel, Raymond; Ulrich, Gilles; Harriman, Anthony
  • New Journal of Chemistry, Vol. 31, Issue 4
  • DOI: 10.1039/b617972j

Structural Control of the Photodynamics of Boron−Dipyrrin Complexes
journal, November 2005

  • Kee, Hooi Ling; Kirmaier, Christine; Yu, Lianhe
  • The Journal of Physical Chemistry B, Vol. 109, Issue 43
  • DOI: 10.1021/jp0525078

Heuristics from Modeling of Spectral Overlap in Förster Resonance Energy Transfer (FRET)
journal, November 2018

  • Qi, Qi; Taniguchi, Masahiko; Lindsey, Jonathan S.
  • Journal of Chemical Information and Modeling, Vol. 59, Issue 2
  • DOI: 10.1021/acs.jcim.8b00753

Fluorescent dyes with large Stokes shifts for super-resolution optical microscopy of biological objects: a review
journal, October 2015

  • Sednev, Maksim V.; Belov, Vladimir N.; Hell, Stefan W.
  • Methods and Applications in Fluorescence, Vol. 3, Issue 4
  • DOI: 10.1088/2050-6120/3/4/042004

9-Acylation of 1-Acyldipyrromethanes Containing a Dialkylboron Mask for the α-Acylpyrrole Motif
journal, November 2004

  • Zaidi, Syeda Huma H.; Muthukumaran, Kannan; Tamaru, Shun-ichi
  • The Journal of Organic Chemistry, Vol. 69, Issue 24
  • DOI: 10.1021/jo048587d