Colorful 4,4-Bipyridine–Squaric Acid Multicomponent Complexes with Varying Degrees of Proton Transfer: Exploring the Nature of New Form IV in the Salt Co-Crystal Continuum

Stevens, Joanna S.

doi:10.1021/acs.cgd.1c01290

Colorful 4,4-Bipyridine–Squaric Acid Multicomponent Complexes with Varying Degrees of Proton Transfer: Exploring the Nature of New Form IV in the Salt Co-Crystal Continuum

Journal Article · 15 December 2021 · Crystal Growth and Design

DOI:https://doi.org/10.1021/acs.cgd.1c01290· OSTI ID:1981819

^[1]

The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.; School of Chemical Engineering & Analytical Science, The University of Manchester, Oxford Road, Manchester, M13 9PL, U.K.

Not provided.

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0012704

OSTI ID:: 1981819

Journal Information:: Crystal Growth and Design, Vol. 22, Issue 1; ISSN 1528-7483

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (43)

Natural Colorants: Historical, Processing and Sustainable Prospects Yusuf, Mohd; Shabbir, Mohd; Mohammad, Faqeer Natural Products and Bioprospecting, Vol. 7, Issue 1 https://doi.org/10.1007/s13659-017-0119-9	journal	January 2017
The history of dyes and pigments Abel, A. Colour Design https://doi.org/10.1016/B978-0-08-101270-3.00024-2	book	January 2012
Molecular and Crystal Structures of Polymorphic Organic Dyes and Coloured Organic Compounds Matsumoto, Shinya; Hwang, Jiyong Progress in the Science of Functional Dyes https://doi.org/10.1007/978-981-33-4392-4_6	book	January 2021
Living in the salt-cocrystal continuum: indecisive organic complexes with thermochromic behaviour Jones, Charlotte L.; Skelton, Jonathan M.; Parker, Stephen C. CrystEngComm, Vol. 21, Issue 10 https://doi.org/10.1039/C8CE02066C	journal	January 2019
Molecular insertion regulates the donor-acceptor interactions in cocrystals for the design of piezochromic luminescent materials Zhai, Chunguang; Yin, Xiu; Niu, Shifeng Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-24381-5	journal	July 2021
A time-temperature integrator based on fluorescent and polymorphic compounds Gentili, Denis; Durso, Margherita; Bettini, Cristian Scientific Reports, Vol. 3, Issue 1 https://doi.org/10.1038/srep02581	journal	September 2013
Polymorphism as an additional functionality of materials for technological applications at surfaces and interfaces Gentili, Denis; Gazzano, Massimo; Melucci, Manuela Chemical Society Reviews, Vol. 48, Issue 9 https://doi.org/10.1039/C8CS00283E	journal	January 2019
Color polymorphism in organic crystals Nogueira, Bernardo A.; Castiglioni, Chiara; Fausto, Rui Communications Chemistry, Vol. 3, Issue 1 https://doi.org/10.1038/s42004-020-0279-0	journal	March 2020
Polymorphism in Molecular Solids: An Extraordinary System of Red, Orange, and Yellow Crystals Yu, Lian Accounts of Chemical Research, Vol. 43, Issue 9 https://doi.org/10.1021/ar100040r	journal	September 2010
Solid-State Acid−Base Interactions in Complexes of Heterocyclic Bases with Dicarboxylic Acids: Crystallography, Hydrogen Bond Analysis, and ¹⁵ N NMR Spectroscopy Li, Z. Jane; Abramov, Yuriy; Bordner, Jon Journal of the American Chemical Society, Vol. 128, Issue 25 https://doi.org/10.1021/ja0541332	journal	June 2006
Pharmaceutical Cocrystals and Their Physicochemical Properties Schultheiss, Nate; Newman, Ann Crystal Growth & Design, Vol. 9, Issue 6 https://doi.org/10.1021/cg900129f	journal	June 2009
Salt–cocrystal continuum for photofunction modulation: stimuli-responsive fluorescence color-tuning of pyridine-modified intramolecular charge-transfer dyes and acid complexes Yano, Yoshio; Ono, Toshikazu; Hatanaka, Sou Journal of Materials Chemistry C, Vol. 7, Issue 29 https://doi.org/10.1039/C9TC02524C	journal	January 2019
Neutral, Zwitterion, Ionic Forms of 5‐Aminoisophthalic Acid in Cocrystals, Salts and Their Optical Properties Singh, Munendra Pal; Tarai, Arup; Baruah, Jubaraj Bikash ChemistrySelect, Vol. 4, Issue 19 https://doi.org/10.1002/slct.201901111	journal	May 2019
Tetrabromoterepthalic Acid in Designing Co-crystals and Salts: Modification of Optical Properties and Schottky Barrier Effect Dey, Sanjoy Kumar; Saha, Rajat; Biswas, Susobhan Crystal Growth & Design, Vol. 14, Issue 1 https://doi.org/10.1021/cg4014009	journal	December 2013
Thermochromism. Day, Jesse H. Chemical Reviews, Vol. 63, Issue 1 https://doi.org/10.1021/cr60221a005	journal	February 1963
A Crystallographic Study on the Thermochromism of Salicylideneanilines Ogawa, Keiichiro; Fujiwara, Toshikatsu; Harada, Jun Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals, Vol. 344, Issue 1 https://doi.org/10.1080/10587250008023832	journal	June 2000
Optical Properties, Thermochromism, and Crystal Structures of the Dimorphs of 2-Iodoanilinium Picrate Tanaka, Masashi; Matsui, Hiroaki; Mizoguchi, Jun-ichi Bulletin of the Chemical Society of Japan, Vol. 67, Issue 6 https://doi.org/10.1246/bcsj.67.1572	journal	June 1994
Turning colour on and off using molecular disorder and proton transfer in multi-component molecular complexes Jones, Charlotte L.; Wilson, Chick C.; Thomas, Lynne H. CrystEngComm, Vol. 16, Issue 26 https://doi.org/10.1039/C4CE00229F	journal	January 2014
Fine-Tuning the Colors of Natural Pigment Emodin with Superior Stability through Cocrystal Engineering Li, Meiqi; Li, Zhen; Zhang, Qi Crystal Growth & Design, Vol. 18, Issue 10 https://doi.org/10.1021/acs.cgd.8b01002	journal	September 2018
Proton-Transfer-Dependent Reversible Phase Changes in the 4,4′-Bipyridinium Salt of Squaric Acid Reetz, Manfred T.; Höger, Sigurd; Harms, Klaus Angewandte Chemie International Edition in English, Vol. 33, Issue 2 https://doi.org/10.1002/anie.199401811	journal	February 1994
Temperature- and Pressure-Induced Proton Transfer in the 1:1 Adduct Formed between Squaric Acid and 4,4′-Bipyridine Martins, David M. S.; Middlemiss, Derek S.; Pulham, Colin R. Journal of the American Chemical Society, Vol. 131, Issue 11 https://doi.org/10.1021/ja8082973	journal	March 2009
The Salt−Cocrystal Continuum: The Influence of Crystal Structure on Ionization State Childs, Scott L.; Stahly, G. Patrick; Park, Aeri Molecular Pharmaceutics, Vol. 4, Issue 3 https://doi.org/10.1021/mp0601345	journal	April 2007
Acid–base crystalline complexes and the pKa rule Cruz-Cabeza, Aurora J. CrystEngComm, Vol. 14, Issue 20 https://doi.org/10.1039/c2ce26055g	journal	January 2012
In Situ Solid-State Reactions Monitored by X-ray Absorption Spectroscopy: Temperature-Induced Proton Transfer Leads to Chemical Shifts Stevens, Joanna S.; Walczak, Monika; Jaye, Cherno Chemistry - A European Journal, Vol. 22, Issue 44 https://doi.org/10.1002/chem.201603822	journal	September 2016
NEXAFS Spectroscopy Stöhr, Joachim Springer Series in Surface Sciences https://doi.org/10.1007/978-3-662-02853-7	book	January 1992
A Review about Regulatory Status and Recent Patents of Pharmaceutical Co-Crystals Kumar, Arun; Kumar, Sandeep; Nanda, Arun Advanced Pharmaceutical Bulletin, Vol. 8, Issue 3 https://doi.org/10.15171/apb.2018.042	journal	August 2018
Pharmaceutical Cocrystals: Regulatory and Strategic Aspects, Design and Development Gadade, Dipak Dilip; Pekamwar, Sanjay Sudhakar Advanced Pharmaceutical Bulletin, Vol. 6, Issue 4 https://doi.org/10.15171/apb.2016.062	journal	December 2016
Proton transfer and hydrogen bonding in the organic solid state: a combined XRD/XPS/ssNMR study of 17 organic acid–base complexes Stevens, Joanna S.; Byard, Stephen J.; Seaton, Colin C. Phys. Chem. Chem. Phys., Vol. 16, Issue 3 https://doi.org/10.1039/C3CP53907E	journal	January 2014
Crystallography Aided by Atomic Core-Level Binding Energies: Proton Transfer versus Hydrogen Bonding in Organic Crystal Structures Stevens, Joanna S.; Byard, Stephen J.; Seaton, Colin C. Angewandte Chemie International Edition, Vol. 50, Issue 42 https://doi.org/10.1002/anie.201103981	journal	September 2011
Characterization of Proton Transfer in Co-Crystals by X-ray Photoelectron Spectroscopy (XPS) Stevens, Joanna S.; Byard, Stephen J.; Schroeder, Sven L. M. Crystal Growth & Design, Vol. 10, Issue 3 https://doi.org/10.1021/cg901481q	journal	March 2010
Salt or Co-Crystal? Determination of Protonation State by X-Ray Photoelectron Spectroscopy (XPS) Stevens, Joanna S.; Byard, Stephen J.; Schroeder, Sven L. M. Journal of Pharmaceutical Sciences, Vol. 99, Issue 11 https://doi.org/10.1002/jps.22164	journal	November 2010
Identification of Protonation State by XPS, Solid-State NMR, and DFT: Characterization of the Nature of a New Theophylline Complex by Experimental and Computational Methods Stevens, Joanna S.; Byard, Stephen J.; Muryn, Christopher A. The Journal of Physical Chemistry B, Vol. 114, Issue 44 https://doi.org/10.1021/jp106465u	journal	November 2010
Chemical Speciation and Bond Lengths of Organic Solutes by Core-Level Spectroscopy: pH and Solvent Influence on p -Aminobenzoic Acid Stevens, Joanna S.; Gainar, Adrian; Suljoti, Edlira Chemistry - A European Journal, Vol. 21, Issue 19 https://doi.org/10.1002/chem.201405635	journal	March 2015
Core level spectroscopies locate hydrogen in the proton transfer pathway – identifying quasi-symmetrical hydrogen bonds in the solid state Stevens, Joanna S.; Coultas, Sarah; Jaye, Cherno Physical Chemistry Chemical Physics, Vol. 22, Issue 9 https://doi.org/10.1039/C9CP05677G	journal	January 2020
Proton Transfer, Hydrogen Bonding, and Disorder: Nitrogen Near-Edge X-ray Absorption Fine Structure and X-ray Photoelectron Spectroscopy of Bipyridine–Acid Salts and Co-crystals Stevens, Joanna S.; Newton, Lauren K.; Jaye, Cherno Crystal Growth & Design, Vol. 15, Issue 4 https://doi.org/10.1021/cg5018278	journal	March 2015
Quantitative analysis of saccharides by X-ray photoelectron spectroscopy Stevens, Joanna S.; Schroeder, Sven L. M. Surface and Interface Analysis, Vol. 41, Issue 6 https://doi.org/10.1002/sia.3047	journal	June 2009
Detection limits in XPS for more than 6000 binary systems using Al and Mg Kα X-rays: XPS detection limits Shard, Alexander G. Surface and Interface Analysis, Vol. 46, Issue 3 https://doi.org/10.1002/sia.5406	journal	February 2014
Fenamate Cocrystals with 4,4′-Bipyridine: Structural and Thermodynamic Aspects Surov, Artem O.; Simagina, Anna A.; Manin, Nikolay G. Crystal Growth & Design, Vol. 15, Issue 1 https://doi.org/10.1021/cg5012633	journal	November 2014
Polymorphic phase transition and thermal stability in squaric acid (H2C4O4) Lee, Kwang-Sei; Jung Kweon, Jin; Oh, In-Hwan Journal of Physics and Chemistry of Solids, Vol. 73, Issue 7 https://doi.org/10.1016/j.jpcs.2012.02.013	journal	July 2012
Soft X-ray Absorption and X-ray Photoelectron Spectroscopic Study of Tautomerism in Intramolecular Hydrogen Bonds of N -Salicylideneaniline Derivatives Ito, Eisuke; Oji, Hiroshi; Araki, Tohru Journal of the American Chemical Society, Vol. 119, Issue 27 https://doi.org/10.1021/ja9641362	journal	July 1997
Pseudoequivalent Nitrogen Atoms in Aqueous Imidazole Distinguished by Chemical Shifts in Photoelectron Spectroscopy Nolting, Dirk; Ottosson, Niklas; Faubel, Manfred Journal of the American Chemical Society, Vol. 130, Issue 26 https://doi.org/10.1021/ja8022384	journal	July 2008
The Electronic Structure and Electron Correlation Effects Studied by xps Sawatzky, G. A.; Antonides, E. Le Journal de Physique Colloques, Vol. 37, Issue C4 https://doi.org/10.1051/jphyscol:1976419	journal	October 1976
Near-Edge X-Ray-Absorption Fine-Structure Studies of Chemisorbed Hydrocarbons: Bond Lengths with a Ruler Stöhr, J.; Sette, F.; Johnson, Allen L. Physical Review Letters, Vol. 53, Issue 17 https://doi.org/10.1103/PhysRevLett.53.1684	journal	October 1984

Similar Records

Proton Transfer, Hydrogen Bonding, and Disorder: Nitrogen Near-Edge X-ray Absorption Fine Structure and X-ray Photoelectron Spectroscopy of Bipyridine¿Acid Salts and Co-crystals

Journal Article · 2015 · Crystal Growth and Design · OSTI ID:1229301

Stevens, J; Newton, L; Jaye, C; +3 more

Antiferroelectric Phase Transition in a Proton-Transfer Salt of Squaric Acid and 2,3-Dimethylpyrazine

Journal Article · 2019 · Journal of the American Chemical Society · OSTI ID:1594225

Lengyel, Jeff; Wang, Xiaoping; Choi, Eun Sang; +16 more

Related Subjects

Chemistry
Crystallography
Materials Science

Colorful 4,4-Bipyridine–Squaric Acid Multicomponent Complexes with Varying Degrees of Proton Transfer: Exploring the Nature of New Form IV in the Salt Co-Crystal Continuum

Citation Formats

References (43)

Similar Records

Related Subjects