The thermo-responsive behavior in molecular crystals of naphthalene diimides and their 3D printed thermochromic composites

Dharmarwardana, Madushani; Arimilli, Bhargav S.; Luzuriaga, Michael A.; Kwon, Sunah; Lee, Hamilton; Appuhamillage, Gayan A.; McCandless, Gregory T.; Smaldone, Ronald A.; Gassensmith, Jeremiah J.

doi:10.1039/C8CE00798E

Title: The thermo-responsive behavior in molecular crystals of naphthalene diimides and their 3D printed thermochromic composites

Journal Article · 07 October 2018 · CrystEngComm

DOI: https://doi.org/10.1039/C8CE00798E · OSTI ID:1463917

^[1]; Arimilli, Bhargav S. ^[1];

^[1]; Kwon, Sunah ^[2];

^[1]; Appuhamillage, Gayan A. ^[1]; McCandless, Gregory T. ^[1];

^[1];

^[3]

Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, USA
Department of Material Science and Engineering, University of Texas at Dallas, Richardson, USA
Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, USA, Department of Biomedical Engineering

Alteration of the number of carbon atoms on the alkoxyphenyl substituent in naphthalene diimides results in tunable thermo-salient behavior.

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Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

OSTI ID:: 1463917

Journal Information:: CrystEngComm, Journal Name: CrystEngComm Journal Issue: 39 Vol. 20; ISSN CRECF4; ISSN 1466-8033

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (54)

Reversible Thermochromic Polymeric Thin Films Made of Ultrathin 2D Crystals of Coordination Polymers Based on Copper(I)-Thiophenolates Troyano, Javier; Castillo, Oscar; Martínez, José I. Advanced Functional Materials, Vol. 28, Issue 5 https://doi.org/10.1002/adfm.201704040	journal	December 2017
In Situ Modification of Metal-Organic Frameworks in Mixed-Matrix Membranes Denny, Michael S.; Cohen, Seth M. Angewandte Chemie, Vol. 127, Issue 31 https://doi.org/10.1002/ange.201504077	journal	June 2015
Photomobile Polymer Materials: Towards Light-Driven Plastic Motors Yamada, Munenori; Kondo, Mizuho; Mamiya, Jun-ichi Angewandte Chemie International Edition, Vol. 47, Issue 27 https://doi.org/10.1002/anie.200800760	journal	June 2008
Polymorphism Versus Thermochromism: Interrelation of Color and Conformation in Overcrowded Bistricyclic Aromatic Enes Biedermann, P. Ulrich; Stezowski, John J.; Agranat, Israel Chemistry - A European Journal, Vol. 12, Issue 12 https://doi.org/10.1002/chem.200501118	journal	April 2006
Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives Takeda, Takashi; Akutagawa, Tomoyuki Chemistry - A European Journal, Vol. 22, Issue 23 https://doi.org/10.1002/chem.201600794	journal	April 2016
Thermochromism at Room Temperature in Overcrowded Bistricyclic Aromatic Enes: Closely Populated Twisted and Folded Conformations Levy, Amalia; Pogodin, Sergey; Cohen, Shmuel European Journal of Organic Chemistry, Vol. 2007, Issue 31 https://doi.org/10.1002/ejoc.200700414	journal	November 2007
Additive manufacturing: technology, applications and research needs Guo, Nannan; Leu, Ming C. Frontiers of Mechanical Engineering, Vol. 8, Issue 3 https://doi.org/10.1007/s11465-013-0248-8	journal	May 2013
Thermochromism and photochromism of N-salicylidenebenzylamines and N-salicylidene-2-aminomethylpyridine Lambi, E.; Gegiou, D.; Hadjoudis, E. Journal of Photochemistry and Photobiology A: Chemistry, Vol. 86, Issue 1-3 https://doi.org/10.1016/1010-6030(94)03943-O	journal	February 1995
Bisimide-lactamimide ring contraction in six-membered polyimides Fomine, Serguei; Fomina, Lioudmila; Arreola, Rogelio Polymer, Vol. 40, Issue 8 https://doi.org/10.1016/S0032-3861(98)00431-5	journal	April 1999
The crystalline-state photochromism, thermochromism and X-ray structural characterization of a new spiroxazine Suh, Hee-Jung; Lim, Woo-Taik; Cui, Jian-Zhong Dyes and Pigments, Vol. 57, Issue 2 https://doi.org/10.1016/S0143-7208(02)00124-9	journal	May 2003
Solid state photochromism and thermochromism of two related N-salicylidene anilines Avadanei, Mihaela; Cozan, Vasile; Shova, Sergiu Chemical Physics, Vol. 444 https://doi.org/10.1016/j.chemphys.2014.10.007	journal	November 2014
Synthesis and reversible thermochromism of azobenzene-containing polydiacetylenes Yu, Xiaowu; Luo, Yanhua; Wu, Wenxuan European Polymer Journal, Vol. 44, Issue 9 https://doi.org/10.1016/j.eurpolymj.2008.05.035	journal	September 2008
Thermochromism of a novel organic compound in the solid state via crystal-to-crystal transformation Lee, Sang Cheol; Jeong, Young Gyu; Jo, Won Ho Journal of Molecular Structure, Vol. 825, Issue 1-3 https://doi.org/10.1016/j.molstruc.2006.04.025	journal	December 2006
Thermochromism of perylenes: Dynamics in aromatics Langhals, Heinz; Kinzel, Simon Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 78, Issue 3 https://doi.org/10.1016/j.saa.2010.12.033	journal	March 2011
Photosalient Behavior of Photoreactive Crystals Medishetty, Raghavender; Sahoo, Subash Chandra; Mulijanto, Caroline Evania Chemistry of Materials, Vol. 27, Issue 5 https://doi.org/10.1021/acs.chemmater.5b00021	journal	February 2015
Mechanical Behavior of Molecular Crystals Induced by Combination of Photochromic Reaction and Reversible Single-Crystal-to-Single-Crystal Phase Transition Kitagawa, Daichi; Kawasaki, Kaito; Tanaka, Rika Chemistry of Materials, Vol. 29, Issue 17 https://doi.org/10.1021/acs.chemmater.7b02558	journal	August 2017
Mechanically Responsive Molecular Crystals Naumov, Panče; Chizhik, Stanislav; Panda, Manas K. Chemical Reviews, Vol. 115, Issue 22 https://doi.org/10.1021/acs.chemrev.5b00398	journal	November 2015
Functional Naphthalene Diimides: Synthesis, Properties, and Applications Al Kobaisi, Mohammad; Bhosale, Sidhanath V.; Latham, Kay Chemical Reviews, Vol. 116, Issue 19 https://doi.org/10.1021/acs.chemrev.6b00160	journal	August 2016
Design Paradigm Utilizing Reversible Diels–Alder Reactions to Enhance the Mechanical Properties of 3D Printed Materials Davidson, Joshua R.; Appuhamillage, Gayan A.; Thompson, Christina M. ACS Applied Materials & Interfaces, Vol. 8, Issue 26 https://doi.org/10.1021/acsami.6b05118	journal	June 2016
Structural, Optical, and Theoretical Studies of a Thermochromic Organic Crystal with Reversibly Variable Second Harmonic Generation Sliwa, Michel; Spangenberg, Arnaud; Malfant, Isabelle Chemistry of Materials, Vol. 20, Issue 12 https://doi.org/10.1021/cm800093a	journal	June 2008
Thermochromic Polymers—Function by Design Seeboth, Arno; Lötzsch, Detlef; Ruhmann, Ralf Chemical Reviews, Vol. 114, Issue 5 https://doi.org/10.1021/cr400462e	journal	January 2014
Thermochromism. Day, Jesse H. Chemical Reviews, Vol. 63, Issue 1 https://doi.org/10.1021/cr60221a005	journal	February 1963
Photoinduced Motions in Azo-Containing Polymers Natansohn, Almeria; Rochon, Paul Chemical Reviews, Vol. 102, Issue 11 https://doi.org/10.1021/cr970155y	journal	November 2002
Thermochromism in Commercial Products White, Mary Anne; LeBlanc, Monique Journal of Chemical Education, Vol. 76, Issue 9 https://doi.org/10.1021/ed076p1201	journal	September 1999
The Thermosalient Phenomenon. “Jumping Crystals” and Crystal Chemistry of the Anticholinergic Agent Oxitropium Bromide Skoko, Željko; Zamir, Sharona; Naumov, Panče Journal of the American Chemical Society, Vol. 132, Issue 40 https://doi.org/10.1021/ja105508b	journal	October 2010
Biomimetic Crystalline Actuators: Structure–Kinematic Aspects of the Self-Actuation and Motility of Thermosalient Crystals Sahoo, Subash Chandra; Panda, Manas K.; Nath, Naba K. Journal of the American Chemical Society, Vol. 135, Issue 33 https://doi.org/10.1021/ja404192g	journal	August 2013
Kinematic and Mechanical Profile of the Self-Actuation of Thermosalient Crystal Twins of 1,2,4,5-Tetrabromobenzene: A Molecular Crystalline Analogue of a Bimetallic Strip Sahoo, Subash Chandra; Sinha, Shashi Bhushan; Kiran, M. S. R. N. Journal of the American Chemical Society, Vol. 135, Issue 37 https://doi.org/10.1021/ja4056323	journal	July 2013
Perpetually Self-Propelling Chiral Single Crystals Panda, Manas K.; Runčevski, Tomče; Husain, Ahmad Journal of the American Chemical Society, Vol. 137, Issue 5 https://doi.org/10.1021/ja5111927	journal	January 2015
Dual Stress and Thermally Driven Mechanical Properties of the Same Organic Crystal: 2,6-Dichlorobenzylidene-4-fluoro-3-nitroaniline Ghosh, Soumyajit; Mishra, Manish Kumar; Ganguly, Somnath Journal of the American Chemical Society, Vol. 137, Issue 31 https://doi.org/10.1021/jacs.5b05324	journal	July 2015
Mechanically Flexible Organic Crystals Achieved by Introducing Weak Interactions in Structure: Supramolecular Shape Synthons Krishna, Gamidi Rama; Devarapalli, Ramesh; Lal, Garima Journal of the American Chemical Society, Vol. 138, Issue 41 https://doi.org/10.1021/jacs.6b05118	journal	August 2016
Optical Activity and Optical Anisotropy in Photomechanical Crystals of Chiral Salicylidenephenylethylamines Takanabe, Akifumi; Tanaka, Masahito; Johmoto, Kohei Journal of the American Chemical Society, Vol. 138, Issue 45 https://doi.org/10.1021/jacs.6b09633	journal	November 2016
Control of Photomechanical Crystal Twisting by Illumination Direction Kitagawa, Daichi; Tsujioka, Hajime; Tong, Fei Journal of the American Chemical Society, Vol. 140, Issue 12 https://doi.org/10.1021/jacs.7b13605	journal	February 2018
New Type of Dual Solid-State Thermochromism: Modulation of Intramolecular Charge Transfer by Intermolecular π−π Interactions, Kinetic Trapping of the Aci-Nitro Group, and Reversible Molecular Locking Naumov, Panče; Lee, Sang Cheol; Ishizawa, Nobuo The Journal of Physical Chemistry A, Vol. 113, Issue 42 https://doi.org/10.1021/jp902517x	journal	October 2009
Directed bending of a polymer film by light Yu, Yanlei; Nakano, Makoto; Ikeda, Tomiki Nature, Vol. 425, Issue 6954 https://doi.org/10.1038/425145a	journal	September 2003
Rapid and reversible shape changes of molecular crystals on photoirradiation Kobatake, Seiya; Takami, Shizuka; Muto, Hiroaki Nature, Vol. 446, Issue 7137 https://doi.org/10.1038/nature05669	journal	April 2007
Colossal positive and negative thermal expansion and thermosalient effect in a pentamorphic organometallic martensite Panda, Manas K.; Runčevski, Tomče; Chandra Sahoo, Subash Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms5811	journal	September 2014
Thermochromism in an organic crystal based on the coexistence of σ- and π-dimers Morita, Yasushi; Suzuki, Shuichi; Fukui, Kozo Nature Materials, Vol. 7, Issue 1 https://doi.org/10.1038/nmat2067	journal	December 2007
Strong and Anomalous Thermal Expansion Precedes the Thermosalient Effect in Dynamic Molecular Crystals Panda, Manas K.; Centore, Roberto; Causà, Mauro Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep29610	journal	July 2016
Chemistry of naphthalene diimides Bhosale, Sheshanath V.; Jani, Chintan H.; Langford, Steven J. Chem. Soc. Rev., Vol. 37, Issue 2 https://doi.org/10.1039/B615857A	journal	January 2008
Actuation based on thermo/photosalient effect: a biogenic smart hybrid driven by light and heat Chandra Sahoo, Subash; Nath, Naba K.; Zhang, Lidong RSC Adv., Vol. 4, Issue 15 https://doi.org/10.1039/C3RA46688D	journal	January 2014
New semiconducting naphthalene bisimides N-substituted with alkoxyphenyl groups: spectroscopic, electrochemical, structural and electrical properties Rybakiewicz, Renata; Tszydel, Izabela; Zapala, Joanna RSC Adv., Vol. 4, Issue 27 https://doi.org/10.1039/C4RA00052H	journal	January 2014
A simple but efficient strategy to enhance hydrostability of intensely fluorescent Mg-based coordination polymer (CP) via forming a composite of CP with hydrophobic PVDF Zhai, Lu; Zhang, Wen-Wei; Zuo, Jing-Lin Dalton Transactions, Vol. 45, Issue 8 https://doi.org/10.1039/C5DT04754D	journal	January 2016
Significant effect of alkyl chain length on fluorescent thermochromism of 9,10-bis(p-alkoxystyryl)anthracenes Xiong, Yao; Ma, Yawen; Yan, Xilong RSC Advances, Vol. 5, Issue 66 https://doi.org/10.1039/C5RA08809G	journal	January 2015
Crystals on the move: mechanical effects in dynamic solids Commins, Patrick; Desta, Israel Tilahun; Karothu, Durga Prasad Chemical Communications, Vol. 52, Issue 97 https://doi.org/10.1039/C6CC06235K	journal	January 2016
Fine-tuning of a thermosalient phase transition by solid solutions Nauha, Elisa; Naumov, Panče; Lusi, Matteo CrystEngComm, Vol. 18, Issue 25 https://doi.org/10.1039/C6CE00762G	journal	January 2016
Metal-coated thermosalient crystals as electrical fuses Khalil, Abdullah; Ahmed, Ejaz; Naumov, Panče Chemical Communications, Vol. 53, Issue 60 https://doi.org/10.1039/C7CC04251E	journal	January 2017
Thermo-mechanically responsive crystalline organic cantilever Dharmarwardana, Madushani; Welch, Raymond P.; Kwon, Sunah Chemical Communications, Vol. 53, Issue 71 https://doi.org/10.1039/C7CC04346E	journal	January 2017
3D printed remendable polylactic acid blends with uniform mechanical strength enabled by a dynamic Diels–Alder reaction Appuhamillage, Gayan A.; Reagan, John C.; Khorsandi, Sina Polymer Chemistry, Vol. 8, Issue 13 https://doi.org/10.1039/C7PY00310B	journal	January 2017
Biodegradable 3D printed polymer microneedles for transdermal drug delivery Luzuriaga, Michael A.; Berry, Danielle R.; Reagan, John C. Lab on a Chip, Vol. 18, Issue 8 https://doi.org/10.1039/C8LC00098K	journal	January 2018
A high frequency photodriven polymer oscillator White, Timothy J.; Tabiryan, Nelson V.; Serak, Svetlana V. Soft Matter, Vol. 4, Issue 9 https://doi.org/10.1039/b805434g	journal	January 2008
Thermally induced and photoinduced mechanical effects in molecular single crystals—a revival Nath, Naba K.; Panda, Manas K.; Sahoo, Subash Chandra CrystEngComm, Vol. 16, Issue 10 https://doi.org/10.1039/c3ce41313f	journal	January 2014
49. Thermochromism and related effects in bixanthenylidenes and bianthronylidenes. Part I. Crystal structure analyses Mills, J. F. D.; Nyburg, S. C. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9630000308	journal	January 1963
High-Speed Electrically Actuated Elastomers with Strain Greater Than 100% Pelrine, Ron; Kornbluh, Roy; Pei, Qibing Science, Vol. 287, Issue 5454, p. 836-839 https://doi.org/10.1126/science.287.5454.836	journal	February 2000
Theoretical investigations of charge carrier transport in organic semiconductors of naphthalene bisimides N-substituted with alkoxyphenyl groups Yin, Jun; Chaitanya, Kadali; Ju, Xue-Hai Canadian Journal of Chemistry, Vol. 93, Issue 7 https://doi.org/10.1139/cjc-2014-0569	journal	July 2015

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