A colorimetric and fluorescent chemosensor for the highly sensitive detection of CO2 gas: experiment and DFT calculation

Abstract A squaraine-based system was developed and demonstrated to fluorescently and colorimetrically sense CO2 gas with high sensitivity in DMSO in the presence of fluoride ion. From results, large hypsochromic shifts were observed both in the absorption spectra (134 nm) and fluorescence spectra (126 nm), and the color change of solution could be clearly observed by the naked eye in response to carbon dioxide gas. Combining 1H NMR titration tests and theoretical calculations, a plausible sensing mechanism that the deprotonated SQ-NH2 with fluoride ion will rapidly restore on condition that acidic carbon dioxide gas bubbles in DMSO is proposed and further revealed. Moreover, theoretical studies agree with experimental data well.

[1]  O. Wolfbeis,et al.  Optical sensing scheme for carbon dioxide using a solvatochromic probe. , 2011, Analytical chemistry.

[2]  S. N. Baker,et al.  Optically responsive switchable ionic liquid for internally-referenced fluorescence monitoring and visual determination of carbon dioxide. , 2012, Chemical communications.

[3]  R. Martínez‐Máñez,et al.  A simple probe for the colorimetric detection of carbon dioxide. , 2013, Chemistry.

[4]  A. Ajayaghosh,et al.  A controlled supramolecular approach toward cation-specific chemosensors: alkaline earth metal ion-driven exciton signaling in squaraine tethered podands. , 2004, Journal of the American Chemical Society.

[5]  Hongming Wang,et al.  Recent advances in carbon dioxide capture, fixation, and activation by using N-heterocyclic carbenes. , 2014, ChemSusChem.

[6]  Ingo Klimant,et al.  Optical Carbon Dioxide Sensors Based on Silicone-Encapsulated Room-Temperature Ionic Liquids , 2007 .

[7]  M. Beller,et al.  Well-defined iron catalyst for improved hydrogenation of carbon dioxide and bicarbonate. , 2012, Journal of the American Chemical Society.

[8]  Jun Feng Zhang,et al.  Recent progress in fluorescent and colorimetric chemosensors for detection of precious metal ions (silver, gold and platinum ions). , 2011, Chemical Society reviews.

[9]  Yu-Lung Lo,et al.  Highly sensitive and linear optical fiber carbon dioxide sensor based on sol–gel matrix doped with silica particles and HPTS , 2009 .

[10]  R. Stuart Haszeldine,et al.  Carbon Capture and Storage: How Green Can Black Be? , 2009, Science.

[11]  Guomin Xia,et al.  Highly sensitive detection of carbon dioxide by a pyrimido[1,2-a]benzimidazole derivative: combining experimental and theoretical studies. , 2015, The Analyst.

[12]  Lei Jiang,et al.  Amidine-based fluorescent chemosensor with high applicability for detection of CO2: a facile way to "see" CO2. , 2013, The Analyst.

[13]  J. F. Stoddart,et al.  A metal-organic framework-based material for electrochemical sensing of carbon dioxide. , 2014, Journal of the American Chemical Society.

[14]  M. Zimmer,et al.  Field-based stable isotope analysis of carbon dioxide by mid-infrared laser spectroscopy for carbon capture and storage monitoring. , 2014, Analytical chemistry.

[15]  Jingbo Lan,et al.  Facile access to extremely efficient energy-transfer pairs via an unexpected reaction of squaraines with ketones. , 2012, Journal of the American Chemical Society.

[16]  A. Ajayaghosh,et al.  A ratiometric fluorescence probe for selective visual sensing of Zn2+. , 2005, Journal of the American Chemical Society.

[17]  E. Bakker,et al.  Direct optical carbon dioxide sensing based on a polymeric film doped with a selective molecular tweezer-type ionophore. , 2012, Analytical chemistry.

[18]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[19]  Juyoung Yoon,et al.  Polydiacetylene-based colorimetric and fluorescent chemosensor for the detection of carbon dioxide. , 2013, Journal of the American Chemical Society.

[20]  Juyoung Yoon,et al.  Anion-activated, thermoreversible gelation system for the capture, release, and visual monitoring of CO2 , 2014, Scientific Reports.

[21]  J. Brennecke,et al.  Recovery of Organic Products from Ionic Liquids Using Supercritical Carbon Dioxide , 2001 .

[22]  Ayusman Sen,et al.  Sensitive colorimetric sensors for visual detection of carbon dioxide and sulfur dioxide , 2015 .

[23]  Zhiqian Guo,et al.  A benzobisimidazolium-based fluorescent and colorimetric chemosensor for CO2. , 2012, Journal of the American Chemical Society.

[24]  B. Tang,et al.  Fluorescent chemosensor for detection and quantitation of carbon dioxide gas. , 2010, Journal of the American Chemical Society.

[25]  Guomin Xia,et al.  A squaraine-based colorimetric and F(-) dependent chemosensor for recyclable CO2 gas detection: highly sensitive off-on-off response. , 2015, Chemical communications.

[26]  Xihan Chen,et al.  Theoretical studies of reactions of carbon dioxide mediated and catalysed by transition metal complexes. , 2012, Chemical communications.

[27]  Juyoung Yoon,et al.  Benzimidazole-embedded N-fused aza-indacenes: synthesis and deprotonation-assisted optical detection of carbon dioxide. , 2013, Chemical communications.

[28]  Ursula E. Spichiger-Keller,et al.  Optical CO2-sensing layers for clinical application based on pH-sensitive indicators incorporated into nanoscopic metal-oxide supports , 2007 .

[29]  M. Nielsen,et al.  Towards a methanol economy based on homogeneous catalysis: methanol to H2 and CO2 to methanol. , 2015, Chemical communications.

[30]  Mohamed Mathlouthi,et al.  Carbonation monitoring of beverage in a laboratory scale unit with on-line measurement of dissolved CO2 , 2006 .

[31]  P. Bühlmann,et al.  Potentiometric sensors based on fluorous membranes doped with highly selective ionophores for carbonate. , 2011, Journal of the American Chemical Society.

[32]  G. Parkin,et al.  Zinc catalysts for on-demand hydrogen generation and carbon dioxide functionalization. , 2012, Journal of the American Chemical Society.

[33]  Christian Krause,et al.  Composite Material for Simultaneous and Contactless Luminescent Sensing and Imaging of Oxygen and Carbon Dioxide , 2006 .

[34]  P. Kortunov,et al.  In Situ Nuclear Magnetic Resonance Mechanistic Studies of Carbon Dioxide Reactions with Liquid Amines in Aqueous Systems: New Insights on Carbon Capture Reaction Pathways , 2015 .

[35]  Colin Finn,et al.  Molecular approaches to the electrochemical reduction of carbon dioxide. , 2012, Chemical communications.

[36]  J. Tomasi,et al.  Ab initio study of solvated molecules: A new implementation of the polarizable continuum model , 1996 .

[37]  I. S. Makarov,et al.  Efficient fluoride-catalyzed conversion of CO2 to CO at room temperature. , 2014, Journal of the American Chemical Society.

[38]  A. Chatterjee,et al.  Fluorescence Turn-on Chemosensor for the Detection of Dissolved CO2 Based on Ion-Induced Aggregation of Tetraphenylethylene Derivative. , 2015, Analytical chemistry.

[39]  Jun Feng Zhang,et al.  Naphthalimide modified rhodamine derivative: ratiometric and selective fluorescent sensor for Cu2+ based on two different approaches. , 2010, Organic letters.

[40]  T. Darwish,et al.  Spiropyran-amidine: a molecular canary for visual detection of carbon dioxide gas. , 2011, Chemistry.

[41]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[42]  A. Cornet,et al.  A new CO2 gas sensing material , 2003 .

[43]  K. Neoh,et al.  CO2-triggered fluorescence “turn-on” response of perylene diimide-containing poly(N,N-dimethylaminoethyl methacrylate) , 2013 .

[44]  E. Bakker,et al.  Non-Severinghaus potentiometric dissolved CO2 sensor with improved characteristics. , 2013, Analytical chemistry.

[45]  D. Gómez‐Díaz,et al.  1-Amine-2-propanol + Triethanolamine Aqueous Blends for Carbon Dioxide Absorption in a Bubble Reactor , 2015 .

[46]  K. Fang,et al.  A simple BODIPY-aniline-based fluorescent chemosensor as multiple logic operations for the detection of pH and CO2 gas. , 2014, Dalton transactions.

[47]  Wei Zhang,et al.  Detection of CO2 in solution with a Pt-NiO solid-state sensor. , 2010, Journal of colloid and interface science.

[48]  Tuğba Davran-Candan.  DFT modeling of CO2 interaction with various aqueous amine structures. , 2014, The journal of physical chemistry. A.

[49]  D. Das,et al.  Fluorescent probes for selective determination of trace level Al3+: recent developments and future prospects , 2013 .

[50]  Jacopo Tomasi,et al.  Geometry optimization of molecular structures in solution by the polarizable continuum model , 1998 .