Nucleophilic addition of phosphorus(iii) derivatives to squaraines: colorimetric detection of transition metal-mediated or thermal reversion

Emily P. Bacher; Antonio J. Lepore; Deisy Pena-Romero; Brandon L. Ashfeld

doi:10.1039/c9cc01243e

journal article Jan 01, 2019

Nucleophilic addition of phosphorus(iii) derivatives to squaraines: colorimetric detection of transition metal-mediated or thermal reversion

Emily P. Bacher Antonio J. Lepore Deisy Pena-Romero Brandon L. Ashfeld

Chemical Communications Vol. 55 No. 22 pp. 3286-3289 · Royal Society of Chemistry (RSC)

View at Publisher Save 10.1039/c9cc01243e

Abstract

Nucleophilic addition of phosphorus(iii) agents to the electrophilic core of intensely colored squaraine dyes gives a bleached zwitterionic adduct in good to excellent yields (up to 99%) at room temperature.

Topics

No keywords indexed for this article. Browse by subject →

References

33

[1]

Treibs Angew. Chem., Int. Ed. (1965) 10.1002/anie.196506941

[2]

Ajayaghosh Acc. Chem. Res. (2005) 10.1021/ar0401000

[3]

Avirah Org. Lett. (2007) 10.1021/ol062691v

[4]

Jyothish Org. Lett. (2004) 10.1021/ol048411y

[5]

Ros-Lis Chem. – Eur. J. (2008) 10.1002/chem.200800300

[6]

Sreejith ACS Nano (2015) 10.1021/acsnano.5b02172

[7]

Harmatys Mol. Pharmaceutics (2013) 10.1021/mp400357v

[8]

Cole Org. Biomol. Chem. (2012) 10.1039/c2ob06783h

[9]

White Bioconjugate Chem. (2010) 10.1021/bc1000998

[10]

Avirah Org. Biomol. Chem. (2012) 10.1039/c1ob06588b

[11]

Prabhakar J. Phys. Chem. C (2010) 10.1021/jp908475n

[12]

Wang Chem. Mater. (2011) 10.1021/cm2020803

[13]

Arunkumar J. Am. Chem. Soc. (2005) 10.1021/ja045760e

[14]

Ros-Lis Chem. Commun. (2002) 10.1039/b206500b

[15]

Ros-Lis J. Am. Chem. Soc. (2004) 10.1021/ja031987i

[16]

Gassensmith Org. Lett. (2008) 10.1021/ol801189a

[17]

Gassensmith Chem. Commun. (2009) 10.1039/b911064j

[18]

Houk Tetrahedron (2008) 10.1016/j.tet.2008.04.105

[19]

Hewage J. Am. Chem. Soc. (2009) 10.1021/ja904045n

[20]

Vaughan J. Am. Chem. Soc. (2013) 10.1021/ja3105279

[21]

Tirla Angew. Chem., Int. Ed. (2016) 10.1002/anie.201608779

[22]

Sub-diffraction-limit imaging by stochastic optical reconstruction microscopy (STORM)

Michael J Rust, Mark Bates, Xiaowei Zhuang

Nature Methods 2006 10.1038/nmeth929

[23]

Imaging Intracellular Fluorescent Proteins at Nanometer Resolution

Eric Betzig, George H. Patterson, Rachid Sougrat et al.

Science 2006 10.1126/science.1127344

[24]

Ultra-High Resolution Imaging by Fluorescence Photoactivation Localization Microscopy

Samuel T. Hess, Thanu P.K. Girirajan, Michael D. Mason

Biophysical Journal 2006 10.1529/biophysj.106.091116

[25]

Eckert Org. Lett. (2018) 10.1021/acs.orglett.8b00656

[26]

Rodriguez Org. Lett. (2016) 10.1021/acs.orglett.6b02122

[27]

Wilson Tetrahedron (2015) 10.1016/j.tet.2015.06.004

[28]

Phosphine-mediated addition of 1,2-dicarbonyls to diazenes: an umpolung approach toward N-acyl hydrazone synthesis

Kasey C. Haugen, Kevin X. Rodriguez, Aditi P. Chavannavar et al.

Tetrahedron Letters 2015 10.1016/j.tetlet.2015.01.030

[29]

Chavannavar Chem. Commun. (2014) 10.1039/c4cc05044d

[30]

Kaur Coord. Chem. Rev. (2018) 10.1016/j.ccr.2017.12.002

[31]

Chen Synth. Met. (2014) 10.1016/j.synthmet.2014.02.018

[32]

Yang J. Mater. Chem. A (2016) 10.1039/c6ta08684e

[33]

Galliani Adv. Opt. Mater. (2015) 10.1002/adom.201500073

Metrics

11

Citations

33

References

Details

Published: Jan 01, 2019
Vol/Issue: 55(22)
Pages: 3286-3289
License: View

Authors

E

Emily P. Bacher

Department of Chemistry and Biochemistry; University of Notre Dame; Notre Dame; USA

A

Antonio J. Lepore

Department of Chemistry and Biochemistry; University of Notre Dame; Notre Dame; USA

D

Deisy Pena-Romero

Department of Chemistry and Biochemistry; University of Notre Dame; Notre Dame; USA

B

Brandon L. Ashfeld

Department of Chemistry and Biochemistry; University of Notre Dame; Notre Dame; USA

Funding

National Institutes of Health Award: T32GM075762

Division of Chemistry Award: 1056242

University of Notre Dame

Cite This Article

Emily P. Bacher, Antonio J. Lepore, Deisy Pena-Romero, et al. (2019). Nucleophilic addition of phosphorus(iii) derivatives to squaraines: colorimetric detection of transition metal-mediated or thermal reversion. Chemical Communications, 55(22), 3286-3289. https://doi.org/10.1039/c9cc01243e

Nucleophilic addition of phosphorus(iii) derivatives to squaraines: colorimetric detection of transition metal-mediated or thermal reversion

You May Also Like