Literature DB >> 30810572

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

Emily P Bacher1, Antonio J Lepore1, Deisy Pena-Romero1, Bradley D Smith1, Brandon L Ashfeld1.   

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. The process can be reversed by adding specific transition metal complexes with high phosphorous(iii) affinity.

Entities:  

Year:  2019        PMID: 30810572      PMCID: PMC6857784          DOI: 10.1039/c9cc01243e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  24 in total

1.  Synthesis of novel quinaldine-based squaraine dyes: effect of substituents and role of electronic factors.

Authors:  Kuthanapillil Jyothish; Kalliat T Arun; Danaboyina Ramaiah
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

2.  Chemistry of squaraine-derived materials: near-IR dyes, low band gap systems, and cation sensors.

Authors:  Ayyappanpillai Ajayaghosh
Journal:  Acc Chem Res       Date:  2005-06       Impact factor: 22.384

3.  Discovery and early development of squaraine rotaxanes.

Authors:  Jeremiah J Gassensmith; Jeffrey M Baumes; Bradley D Smith
Journal:  Chem Commun (Camb)       Date:  2009-08-24       Impact factor: 6.222

4.  Phosphorus(III)-Mediated Stereoconvergent Formal [4+1]-Cycloannulation of 1,2-Dicarbonyls and o-Quinone Methides: A Multicomponent Assembly of 2,3-Dihydrobenzofurans.

Authors:  Kevin X Rodriguez; Justin D Vail; Brandon L Ashfeld
Journal:  Org Lett       Date:  2016-09-07       Impact factor: 6.005

5.  Dual-mode semisquaraine-based sensor for selective detection of Hg2+ in a micellar medium.

Authors:  Rekha R Avirah; Kuthanapillil Jyothish; Danaboyina Ramaiah
Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

6.  Water-soluble, deep-red fluorescent squaraine rotaxanes.

Authors:  Erin L Cole; Easwaran Arunkumar; Shuzhang Xiao; Bryan A Smith; Bradley D Smith
Journal:  Org Biomol Chem       Date:  2011-12-08       Impact factor: 3.876

7.  Development of a Photoactivatable Phosphine Probe for Induction of Intracellular Reductive Stress with Single-Cell Precision.

Authors:  Alina Tirla; Pablo Rivera-Fuentes
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-20       Impact factor: 15.336

8.  In vivo imaging of bone using a deep-red fluorescent molecular probe bearing multiple iminodiacetate groups.

Authors:  Kara M Harmatys; Erin L Cole; Bradley D Smith
Journal:  Mol Pharm       Date:  2013-10-22       Impact factor: 4.939

9.  Pattern-based recognition of thiols and metals using a single squaraine indicator.

Authors:  Himali S Hewage; Eric V Anslyn
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

10.  Phosphine quenching of cyanine dyes as a versatile tool for fluorescence microscopy.

Authors:  Joshua C Vaughan; Graham T Dempsey; Eileen Sun; Xiaowei Zhuang
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

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  2 in total

1.  A Phosphine-Mediated Dearomative Skeletal Rearrangement of Dianiline Squaraine Dyes.

Authors:  Emily P Bacher; Kevin J Koh; Antonio J Lepore; Allen G Oliver; Olaf Wiest; Brandon L Ashfeld
Journal:  Org Lett       Date:  2021-03-26       Impact factor: 6.005

Review 2.  Cationic Organophosphorus Chromophores: A Diamond in the Rough among Ionic Dyes.

Authors:  Andrey Belyaev; Pi-Tai Chou; Igor O Koshevoy
Journal:  Chemistry       Date:  2020-10-30       Impact factor: 5.020

  2 in total

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