Diketopyrrolopyrrole: brilliant red pigment dye-based fluorescent probes and their applications.

The development of fluorescent probes for the detection of biologically relevant species is a burgeoning topic in the field of supramolecular chemistry. A number of available dyes such as rhodamine, coumarin, fluorescein, and cyanine have been employed in the design and synthesis of new fluorescent probes. However, diketopyrrolopyrrole (DPP) and its derivatives have a distinguished role in supramolecular chemistry for the design of fluorescent dyes. DPP dyes offer distinctive advantages relative to other organic dyes, including high fluorescence quantum yields and good light and thermal stability. Significant advancements have been made in the development of new fluorescent probes based on DPP in recent years as a result of tireless research efforts by the chemistry scientific community. In this tutorial review, we highlight the recent progress in the development of DPP-based fluorescent probes for the period spanning 2009 to the present time and the applications of these probes to recognition of biologically relevant species including anions, cations, reactive oxygen species, thiols, gases and other miscellaneous applications. This review is targeted toward providing the readers with deeper understanding for the future design of DPP-based fluorogenic probes for chemical and biological applications.

[1]  Matinder Kaur,et al.  Dual channel receptor based on diketopyrrolopyrrole alkyne conjugate for detection of Hg2+/Cu2+ by “naked eye” and fluorescence , 2014 .

[2]  Hiroo Takahashi,et al.  Polymorph of 1,4-diketo-3,6-bis-(4′-dipyridyl)-pyrrolo-[3,4-c]pyrrole and their hydrogen bond network: A material for H2 gas sensor , 2006 .

[3]  Kaibo Zheng,et al.  Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging. , 2013, Chemical Society Reviews.

[4]  J. Yu,et al.  A new diketopyrrolopyrrole (DPP) derivative bearing boronate group as fluorescent probe for fluoride ion , 2013 .

[5]  P. Raghunath,et al.  An Acid–Base Controllable Hierarchical Nanostructure from a NIR-Absorbing Conjugated Polyrotaxane-Based Optical Molecular Switch , 2013 .

[6]  M. Drobizhev,et al.  Strong two-photon absorption enhancement in a unique bis-porphyrin bearing a diketopyrrolopyrrole unit. , 2013, Chemical communications.

[7]  H. Tian,et al.  Colorimetric and ratiometric red fluorescent chemosensor for fluoride ion based on diketopyrrolopyrrole. , 2010, Organic letters.

[8]  I. Klimant,et al.  Diketo-pyrrolo-pyrrole dyes as new colorimetric and fluorescent pH indicators for optical carbon dioxide sensors. , 2013, Analytical chemistry.

[9]  Donghoon Choi,et al.  Chemodosimeter approach: Selective detection of fluoride ion using a diketopyrrolopyrrole derivative , 2014 .

[10]  I. Klimant,et al.  Fluorescent materials for pH sensing and imaging based on novel 1,4-diketopyrrolo-[3,4-c]pyrrole dyes , 2013, Journal of materials chemistry. C.

[11]  Kuan Liu,et al.  Synthesis and surfactochromicity of 1,4‐diketopyrrolo[3,4‐c]pyrrole(DPP)‐based anionic conjugated polyelectrolytes , 2014 .

[12]  J. Hua,et al.  Diketopyrrolopyrrole-based fluorescent conjugated polymer for application of sensing fluoride ion and bioimaging , 2014 .

[13]  J. Yu,et al.  Mild synthesis and photophysical properties of symmetrically substituted diketopyrrolopyrrole derivatives , 2014 .

[14]  J. Vyňuchal,et al.  Study of phenylpyridyldiketopyrrolopyrrole interaction with hydrogen in gas and in acids , 2010 .

[15]  Z. Hao,et al.  Some aspects of organic pigments , 1997 .

[16]  Hiroo Takahashi,et al.  Carrier generation and carrier determination in dipyridyldiketopyrrolopyrrole-based H2 gas sensors , 2006 .

[17]  A. Zumbusch,et al.  Near-infrared dyes and fluorophores based on diketopyrrolopyrroles. , 2007, Angewandte Chemie.

[18]  J. Nicoud,et al.  Water-soluble diketopyrrolopyrrole derivatives for two-photon excited fluorescence microscopy , 2013 .

[19]  A. Zumbusch,et al.  Selective NIR chromophores: bis(pyrrolopyrrole) cyanines. , 2011, Angewandte Chemie.

[20]  T. Stokłosa,et al.  Bright, color-tunable fluorescent dyes based on π-expanded diketopyrrolopyrroles. , 2012, Organic letters.

[21]  Michael Schäferling,et al.  The art of fluorescence imaging with chemical sensors. , 2012, Angewandte Chemie.

[22]  Arben Merkoçi,et al.  Recent trends in macro-, micro-, and nanomaterial-based tools and strategies for heavy-metal detection. , 2011, Chemical reviews.

[23]  J. Nicoud,et al.  Functionalized two-photon absorbing diketopyrrolopyrrole-based fluorophores for living cells fluorescent microscopy. , 2013, Bioconjugate chemistry.

[24]  Erlong Zhang,et al.  A review of NIR dyes in cancer targeting and imaging. , 2011, Biomaterials.

[25]  Y. Araki,et al.  Pyrrolopyrrole aza-BODIPY analogues: a facile synthesis and intense fluorescence. , 2013, Chemical communications.

[26]  M. V. R. Raju,et al.  A novel diketopyrrolopyrrole (DPP)-based [2]rotaxane for highly selective optical sensing of fluoride. , 2013, Organic letters.

[27]  J. Yu,et al.  A new turn-on fluorescent chemosensor based on diketopyrrolopyrrole (DPP) for imaging Zn2+ in living cells. , 2013, The Analyst.

[28]  W. Jang,et al.  A diketopyrrolopyrrole-based colorimetric and fluorescent probe for cyanide detection. , 2012, Chemistry, an Asian journal.

[29]  Yan Li Zhang,et al.  Diphenylamine end-capped 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) derivatives with large two-photon absorption cross-sections and strong two-photon excitation red fluorescence. , 2009, Chemical communications.

[30]  Shaomin Ji,et al.  Colorimetric and ratiometric fluorescent chemosensor based on diketopyrrolopyrrole for selective detection of thiols: an experimental and theoretical study. , 2011, The Journal of organic chemistry.

[31]  E. Zendri,et al.  New 3,6-bis(biphenyl)diketopyrrolopyrrole dyes and pigments via Suzuki-Miyaura coupling , 2013 .

[32]  Baoliang Zhang,et al.  Two-photon absorption and fluorescence fluoride-sensing properties of N-octyl-3,6-bis[4-(4-(diphenylamino)phenyl)phenyl]-1,4-diketo-pyrrolo[3,4-c]pyrrole , 2014 .

[33]  K. Lee,et al.  Diketopyrrolopyrrole: A versatile building block for organic photovoltaic materials , 2013, Macromolecular Research.

[34]  Baoliang Zhang,et al.  N-Monoalkylated 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrroles as effective one- and two-photon fluorescence chemosensors for fluoride anions , 2013 .

[35]  Kihang Choi,et al.  A fluorescence turn-on and colorimetric probe based on a diketopyrrolopyrrole–tellurophene conjugate for efficient detection of hydrogen peroxide and glutathione , 2014 .

[36]  T. Kanbara,et al.  Synthesis of highly fluorescent diketopyrrolopyrrole derivative and two-step response of fluorescence to acid , 2010 .

[37]  J. Yu,et al.  New diketopyrrolopyrrole (DPP) derivative as fluorescent probe for Zn2 , 2013 .

[38]  H. Tian,et al.  Synthesis and two‐photon absorption properties of hyperbranched diketo‐pyrrolo‐pyrrole polymer with triphenylamine as the core , 2009 .

[39]  Huimin Ma,et al.  Design strategies for water-soluble small molecular chromogenic and fluorogenic probes. , 2014, Chemical reviews.

[40]  D. Qu,et al.  A red-emission diketopyrrolopyrrole-based fluoride ion chemosensor with high contrast ratio working in a dual mode: Solvent-dependent ratiometric and “turn on” pathways , 2012 .

[41]  A. Zumbusch,et al.  Pyrrolopyrrole cyanine dyes: a new class of near-infrared dyes and fluorophores. , 2009, Chemistry.

[42]  R. Beuerman,et al.  Synthesis of diketopyrrolopyrrole‐containing conjugated polyelectrolytes for naked‐eye detection of DNA , 2011 .

[43]  Lidong Li,et al.  Water‐Soluble Conjugated Polymers for Amplified Fluorescence Detection of Template‐Independent DNA Elongation Catalyzed by Polymerase , 2011 .

[44]  C. B. Nielsen,et al.  Recent Advances in the Development of Semiconducting DPP‐Containing Polymers for Transistor Applications , 2013, Advanced materials.

[45]  Prashant Sonar,et al.  High mobility diketopyrrolopyrrole (DPP)-based organic semiconductor materials for organic thin film transistors and photovoltaics , 2013 .

[46]  F. Würthner,et al.  Synthesis and characterization of optical and redox properties of bithiophene-functionalized diketopyrrolopyrrole chromophores. , 2011, The Journal of organic chemistry.

[47]  Lin Li,et al.  Sensitive detection of DNA by hyperbranched diketopyrrolopyrrole-based conjugated polyelectrolytes , 2013 .

[48]  R. Lenz,et al.  DPP chemistry — continuous innovation , 2002 .

[49]  A. Zumbusch,et al.  Water-soluble pyrrolopyrrole cyanine (PPCy) NIR fluorophores. , 2014, Chemical communications.