Photoinduced Proton Transfer between Photoacid and pH‐Sensitive Dyes: Influence Factors and Application for Visible‐Light‐Responsive Rewritable Paper

Ink‐free printing based on rewritable paper is an efficient and environmental friendly way to reuse paper, protect resources, and save energy for sustainable development of human society. Among various kinds of rewritable media, light responsive rewritable paper (LRP) is one of the most popular research areas due to its clean and favorable noncontact writing. Visible light is more suitable for LRP for its superior penetration and much less damages to organic molecules than UV light. However, visible‐light‐responsive rewritable paper (VLRP) has only limited successes so far. Herein, a VLRP is newly designed and fabricated based on photoinduced proton transfer (PPT) between photoacid and pH‐sensitive dyes. Success of it is highly benefited from systematical investigation and in‐depth understanding on the key influence factors, such as concentration‐induced undesired isomerization, temperature, humidity, and light intensity, on the PPT and its inverse process. As‐prepared VLRP shows long‐awaited properties, such as, high color contrast and resolution, appropriate legible time of prints, excellent reversibility (>100 cycles), easiness to achieve multicolor prints, and agreeing well with environmental concept of green printing. In addition, study of influence factors on PPT in this work, to some extent, may also help people understand complex photocycle process in biosystem.

[1]  P. Winston,et al.  Saturated Solutions For the Control of Humidity in Biological Research , 1960 .

[2]  J. Lanyi,et al.  Water is required for proton transfer from aspartate-96 to the bacteriorhodopsin Schiff base. , 1991, Biochemistry.

[3]  J. Jacobson,et al.  An electrophoretic ink for all-printed reflective electronic displays , 1998, Nature.

[4]  E. Kenndler,et al.  Ionization constants of weak acids and bases in organic solvents. , 1999, Journal of biochemical and biophysical methods.

[5]  N. Tamaoki,et al.  Rewritable Full‐Color Recording in a Photon Mode , 2000 .

[6]  B. J. Feenstra,et al.  Video-speed electronic paper based on electrowetting , 2003, Nature.

[7]  S. Hirano,et al.  A photon‐mode full‐color rewritable image using photochromic compounds , 2004 .

[8]  Takuzo Aida,et al.  Rewritable phosphorescent paper by the control of competing kinetic and thermodynamic self-assembling events , 2005, Nature materials.

[9]  John R. Reynolds,et al.  Electrochromic organic and polymeric materials for display applications , 2006, Displays.

[10]  J. Lanyi,et al.  Proton transfers in the bacteriorhodopsin photocycle. , 2006, Biochimica et biophysica acta.

[11]  Hoi Sing Kwok,et al.  60.1: Optical Rewritable Electronic Paper with Fluorescent Dye Doped Liquid Crystal , 2008 .

[12]  T. Mizokuro,et al.  Writable and erasable PPV medium by irradiation at 365 nm , 2008 .

[13]  Y. Ueda,et al.  Reversible coloring/decoloring reaction of leuco dye controlled by long-chain molecule , 2008 .

[14]  Norihisa Kobayashi,et al.  Organic electrochromism for a new color electronic paper , 2008 .

[15]  Hoi Sing Kwok,et al.  Light Printing of Grayscale Pixel Images on Optical Rewritable Electronic Paper , 2008 .

[16]  S. Kobatake,et al.  Synthesis of photochromic diarylethene polymers for a write-by-light/erase-by-heat recording system , 2008 .

[17]  Kiyotaka Sato,et al.  In Situ Observation of Thermochromic Behavior of Binary Mixtures of Phenolic Long-Chain Molecules and Fluoran Dye for Rewritable Paper Application , 2008 .

[18]  Bartosz A Grzybowski,et al.  Writing self-erasing images using metastable nanoparticle "inks". , 2009, Angewandte Chemie.

[19]  Y. Kohno,et al.  Simple full-color rewritable film with photochromic fulgide derivatives , 2009 .

[20]  Le He,et al.  Rewritable Photonic Paper with Hygroscopic Salt Solution as Ink , 2009 .

[21]  Sunghoon Kwon,et al.  Niche applications of magnetically responsive photonic structures , 2010 .

[22]  K. Ishida,et al.  Reversible multi-coloring reaction of spironaphtooxazine controlled by long-chain molecule , 2010 .

[23]  Jong-Man Kim,et al.  Fabrication of patterned images in photochromic organic microfibers. , 2010, Macromolecular rapid communications.

[24]  D. Strohecker,et al.  Long-lived photoacid based upon a photochromic reaction. , 2011, Journal of the American Chemical Society.

[25]  S. Kobatake,et al.  Photochromic polymers bearing various diarylethene chromophores as the pendant: synthesis, optical properties, and multicolor photochromism , 2011 .

[26]  T. Ogata,et al.  Thermal and Photochemical Control of Molecular Orientation of Azo-Functionalized Polymer Liquid Crystals and Application for Photo-Rewritable Paper. , 2011, Macromolecular rapid communications.

[27]  A. Urbas,et al.  Reversible light-directed red, green, and blue reflection with thermal stability enabled by a self-organized helical superstructure. , 2012, Journal of the American Chemical Society.

[28]  Alexander Afanasyev,et al.  Submicron-scale liquid crystal photo-alignment , 2013 .

[29]  Lan Sheng,et al.  Stress acidulated amphoteric molecules and mechanochromism via reversible intermolecular proton transfer. , 2013, Chemical communications.

[30]  Mingsheng Wang,et al.  Magnetically rewritable photonic ink based on superparamagnetic nanochains , 2013 .

[31]  Valentine K. Johns,et al.  Physicochemical study of a metastable-state photoacid. , 2013, The journal of physical chemistry. A.

[32]  Hoi Sing Kwok,et al.  Autostereoscopic 3D pictures on optically rewritable electronic paper , 2013 .

[33]  Jong-Man Kim,et al.  Rewritable color patterns with photochromic diarylethene-embedded electrospun fibers , 2014 .

[34]  Rafal Klajn,et al.  Spiropyran-based dynamic materials. , 2014, Chemical Society reviews.

[35]  J Sun,et al.  Optically rewritable 3D liquid crystal displays. , 2014, Optics letters.

[36]  Lan Sheng,et al.  Hydrochromic molecular switches for water-jet rewritable paper , 2014, Nature Communications.

[37]  Le He,et al.  Photocatalytic colour switching of redox dyes for ink-free light-printable rewritable paper , 2014, Nature Communications.

[38]  F. Raymo,et al.  Saving paper with switchable ink , 2014 .

[39]  X. Qu,et al.  Polyoxometalate-based Rewritable Paper , 2015 .

[40]  Y. Liao,et al.  Photochromism based on reversible proton transfer , 2015 .

[41]  M. Chi,et al.  Enhanced photoreversible color switching of redox dyes catalyzed by barium-doped TiO2 nanocrystals. , 2015, Angewandte Chemie.

[42]  Xuemin Du,et al.  Water as a colorful ink: transparent, rewritable photonic coatings based on colloidal crystals embedded in chitosan hydrogel , 2015 .

[43]  M. I. Khazi,et al.  Full Color Light Responsive Diarylethene Inks for Reusable Paper , 2016 .

[44]  P. Weis,et al.  Visible-Light-Responsive Azopolymers with Inhibited π–π Stacking Enable Fully Reversible Photopatterning , 2016 .

[45]  Woomin Jeong,et al.  Inkjet‐Printable Amphiphilic Polydiacetylene Precursor for Hydrochromic Imaging on Paper , 2016 .

[46]  Yu-Ai Duan,et al.  Mechanochromic luminogen with aggregation-induced emission: implications for ink-free rewritable paper with high fatigue resistance and low toxicity , 2016 .

[47]  A. Xu,et al.  Oxygen-Deficient TiO2 - x/Methylene Blue Colloids: Highly Efficient Photoreversible Intelligent Ink. , 2016, Langmuir : the ACS journal of surfaces and colloids.

[48]  Y. Liao,et al.  Photocontrolled proton transfer in solution and polymers using a novel photoacid with strong C–H acidity , 2016 .

[49]  R. Barberi,et al.  Rewritable Optical Storage with a Spiropyran Doped Liquid Crystal Polymer Film. , 2016, Macromolecular rapid communications.

[50]  K. Glusac.  What has light ever done for chemistry? , 2016, Nature chemistry.

[51]  J. Hernando,et al.  Temperature-Controlled Switchable Photochromism in Solid Materials. , 2016, Angewandte Chemie.

[52]  Jing Wei,et al.  Electrospun Photochromic Hybrid Membranes for Flexible Rewritable Media. , 2016, ACS applied materials & interfaces.

[53]  J. Micheau,et al.  Switching a pH indicator by a reversible photoacid: A quantitative analysis of a new two-component photochromic system , 2016 .

[54]  Lehui Xiao,et al.  Photoswitchable fluorescent polymeric nanoparticles for rewritable fluorescence patterning and intracellular dual-color imaging with AIE-based fluorogens as FRET donors , 2017 .

[55]  Yaoxin Zhang,et al.  Inkjet-Printable Hydrochromic Paper for Encrypting Information and Anticounterfeiting. , 2017, ACS applied materials & interfaces.

[56]  D. Shen,et al.  Rewritable Painting Realized from Ambient-Sensitive Fluorescence of ZnO Nanoparticles , 2017, Scientific Reports.

[57]  Defang Xu,et al.  Triphenylamine functionalized β-Ketoiminate boron complex exhibiting aggregation-induced emission and mechanofluorochromism , 2017 .

[58]  Cheolmin Park,et al.  Printable and Rewritable Full Block Copolymer Structural Color , 2017, Advanced materials.

[59]  Yi-sheng Liu,et al.  Photocatalytic Color Switching of Transition Metal Hexacyanometalate Nanoparticles for High-Performance Light-Printable Rewritable Paper. , 2017, Nano letters.

[60]  Dan Han,et al.  Photocatalytic Self-Doped SnO2-x Nanocrystals Drive Visible-Light-Responsive Color Switching. , 2017, Angewandte Chemie.