Panchromatic Fluorescence Emission from Thienosquaraines Dyes: White Light Electrofluorochromic Devices
Abstract
:1. Introduction
2. Results and Discussion
2.1. Electrochemical Properties
2.2. Photophysical Properties in Solution
2.3. Photophysical Properties in Device
2.3.1. Photophysical Properties in the off State
2.3.2. Electrofluorochromic Characterization
3. Materials and Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
- Poon, C.-T.; Wu, D.; Lam, W.H.; Yam, V.W.-W. A Solution-Processable Donor–Acceptor Compound Containing Boron(III) Centers for Small-Molecule-Based High-Performance Ternary Electronic Memory Devices. Angew. Chem. Int. Ed. 2015, 54, 10569–10573. [Google Scholar] [CrossRef]
- Chiu, Y.-C.; Sun, H.-S.; Lee, W.-Y.; Halila, S.; Borsali, R.; Chen, W.-C. Oligosaccharide Carbohydrate Dielectrics toward High-Performance Non-volatile Transistor Memory Devices. Adv. Mater. 2015, 27, 6257–6264. [Google Scholar] [CrossRef] [PubMed]
- Raghupathi, K.R.; Guo, J.; Munkhbat, O.; Rangadurai, P.; Thayumanavan, S. Supramolecular Disassembly of Facially Amphiphilic Dendrimer Assemblies in Response to Physical, Chemical, and Biological Stimuli. Acc. Chem. Res. 2014, 47, 2200–2211. [Google Scholar] [CrossRef] [PubMed]
- Molina, M.; Asadian-Birjand, M.; Balach, J.; Bergueiro, J.; Miceli, E.; Calderon, M. Stimuli-responsive nanogel composites and their application in nanomedicine. Chem. Soc. Rev. 2015, 44, 6161–6186. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Hou, X.; Ke, C.; Bruns, C.J.; McGonigal, P.R.; Pettman, R.B.; Stoddart, J.F. Tunable solid-state fluorescent materials for supramolecular encryption. Nat. Commun. 2015, 6, 6884. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Bisoyi, H.K.; Li, Q. Light-Directing Chiral Liquid Crystal Nanostructures: From 1D to 3D. Acc. Chem. Res. 2014, 47, 3184–3195. [Google Scholar] [CrossRef]
- Mutai, T.; Satou, H.; Araki, K. Reproducible on-off switching of solid-state luminescence by controlling molecular packing through heat-mode interconversion. Nat. Mater. 2005, 4, 685–687. [Google Scholar] [CrossRef]
- Yan, D.P.; Lu, J.; Ma, J.; Wei, M.; Evans, D.G.; Duan, X. Reversibly Thermochromic, Fluorescent Ultrathin Films with a Supramolecular Architecture. Angew. Chem. 2011, 123, 746–749. [Google Scholar] [CrossRef]
- Bu, J.; Watanabe, K.; Hayasaka, H.; Akagi, K. Photochemically colour-tuneable white fluorescence illuminants consisting of conjugated polymer nanospheres. Nat. Commun. 2014, 5, 3799. [Google Scholar] [CrossRef] [Green Version]
- Wang, Z.; Ma, Z.; Wang, Y.; Xu, Z.; Luo, Y.; Wei, Y.; Jia, X. A Novel Mechanochromic and Photochromic Polymer Film: When Rhodamine Joins Polyurethane. Adv. Mater. 2015, 27, 6469–6474. [Google Scholar] [CrossRef]
- Gong, Y.; Chen, G.; Peng, Q.; Yuan, W.Z.; Xie, Y.; Li, S.; Zhang, Y.; Tang, B.Z. Achieving Persistent Room Temperature Phosphorescence and Remarkable Mechanochromism from Pure Organic Luminogens. Adv. Mater. 2015, 27, 6195–6201. [Google Scholar] [CrossRef]
- Sagara, Y.; Yamane, S.; Mitani, M.; Weder, C.; Kato, T. Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of Materials. Adv. Mater. 2016, 28, 1073–1076. [Google Scholar] [CrossRef] [PubMed]
- Park, S.K.; Cho, I.; Gierschner, J.; Kim, J.H.; Kwon, J.E.; Kwon, O.K.; Whang, D.R.; Park, J.-H.; An, B.-K.; Park, S.Y. Stimuli-Responsive Reversible Fluorescence Switching in a Crystalline Donor–Acceptor Mixture Film: Mixed Stack Charge-Transfer Emission versus Segregated Stack Monomer Emission. Angew. Chem. Int. Ed. 2016, 55, 203–207. [Google Scholar] [CrossRef]
- Yoon, S.J.; Chung, J.W.; Gierschner, J.; Kim, K.S.; Choi, M.G.; Kim, D.; Park, S.Y. Multistimuli Two-Color Luminescence Switching via Different Slip-Stacking of Highly Fluorescent Molecular Sheets. J. Am. Chem. Soc. 2010, 132, 13675–13683. [Google Scholar] [CrossRef] [PubMed]
- Liou, G.S.; Hsiao, S.H.; Su, T.H. Synthesis, luminescence and electrochromism of aromatic poly(amine–amide)s with pendent triphenylamine moieties. J. Mater. Chem. 2005, 15, 1812–1820. [Google Scholar] [CrossRef]
- Asil, D.; Foster, J.A.; Patra, A.; de Hatte, X.; del Barrio, J.; Scherman, O.A.; Nitschke, J.R.; Friend, R.H. Temperature- and Voltage-Induced Ligand Rearrangement of a Dynamic Electroluminescent Metallopolymer. Angew. Chem. 2014, 126, 8528–8531. [Google Scholar] [CrossRef]
- Guo, S.; Huang, T.; Liu, S.; Zhang, K.Y.; Yang, H.; Han, J.; Zhao, Q.; Huang, W. Luminescent ion pairs with tunable emission colors for light-emitting devices and electrochromic switches. Chem. Sci. 2017, 8, 348–360. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Corrente, G.A.; Fabiano, E.; Manni, F.; Chidichimo, G.; Gigli, G.; Beneduci, A.; Capodilupo, A.-L. Colorless to All-Black Full-NIR High-Contrast Switching in Solid Electrochromic Films Prepared with Organic Mixed Valence Systems Based on Dibenzofulvene Derivatives. Chem. Mater. 2018, 30, 5610–5620. [Google Scholar] [CrossRef]
- Veltri, L.; Cavallo, G.; Beneduci, A.; Metrangolo, P.; Corrente, G.A.; Ursini, M.; Romeo, R.; Terraneo, G.; Gabriele, B. Synthesis and thermotropic properties of new green electrochromic ionic liquid crystals. New J. Chem. 2019, 43, 18285–18293. [Google Scholar] [CrossRef]
- Corrente, G.A.; Fabiano, E.; La Deda, M.; Manni, F.; Gigli, G.; Chidichimo, G.; Capodilupo, A.L.; Beneduci, A. High-Performance Electrofluorochromic Switching Devices Using a Novel Arylamine-Fluorene Redox-Active Fluorophore. ACS Appl. Mater. Interfaces 2019, 11, 12202–12208. [Google Scholar] [CrossRef]
- Corrente, G.A.; Cospito, S.; Capodilupo, A.L.; Beneduci, A. Mixed-Valence Compounds as a New Route for Electrochromic Devices with High Coloration Efficiency in the Whole Vis-NIR Region. Appl. Sci. 2020, 10, 8372. [Google Scholar] [CrossRef]
- Audebert, P.; Miomandre, F. Electrofluorochromism: From molecular systems to set-up and display. Chem. Sci. 2013, 4, 575–584. [Google Scholar] [CrossRef]
- Seo, S.; Kim, Y.; Zhou, Q.; Clavier, G.; Audebert, P.; Kim, E. White Electrofluorescence Switching from Electrochemically Convertible Yellow Fluorescent Dyad. Adv. Funct. Mater. 2012, 22, 3556–3561. [Google Scholar] [CrossRef]
- Al-Kutubi, H.; Zafarani, H.R.; Rassaei, L.; Mathwig, K. Electrofluorochromic Systems: Molecules and Materials Exhibiting Redox-Switchable Fluorescence. Eur. Polym. J. 2016, 83, 478–498. [Google Scholar] [CrossRef]
- Treibs, A.; Jacob, K. Cyclotrimethine dyes derived from squaric acid. Angew. Chem., Int. Ed. Engl. 1965, 4, 694. [Google Scholar] [CrossRef]
- Beverina, L.; Salice, P. Squaraine compounds: Tailored design and synthesis towards a variety of material science applications. Eur. J. Org. Chem. 2010, 2010, 1207–1225. [Google Scholar] [CrossRef]
- Xia, G.; Wang, H. Squaraine dyes: The hierarchical synthesis and its application in optical detection. J. Photoch. Photobio. C 2017, 31, 84–113. [Google Scholar] [CrossRef]
- He, J.; Jo, Y.J.; Sun, X.; Qiao, W.; Ok, J.; Kim, T. Squaraine Dyes for Photovoltaic and Biomedical Applications. Adv. Funct. Mater. 2021, 31, 2008201. [Google Scholar] [CrossRef]
- Ilina, K.; MacCuaig, W.M.; Laramie, M.; Jeouty, J.N.; McNally, L.R.; Henary, M. Squaraine Dyes: Molecular Design for Different Applications and Remaining Challenges. Bioconjugate Chem. 2020, 31, 194–213. [Google Scholar] [CrossRef]
- Chen, G.; Sasabe, H.; Igarashi, T.; Hong, Z.; Kido, J. Squaraine dyes for organic photovoltaic cells. J. Mater. Chem. A 2015, 3, 14517–14534. [Google Scholar] [CrossRef]
- Chen, Y.; Zhu, W.; Wu, J.; Huang, Y.; Facchetti, A.; Marks, T.J. Recent Advances in Squaraine Dyes for Bulk-Heterojunction Organic Solar Cells. Org. Photonics Photovolt. 2019, 7, 1–16. [Google Scholar] [CrossRef]
- Chang, H.J.; Bondar, M.V.; Liu, T.; Liu, X.; Singh, S.; Belfield, K.D.; Sheely, A.; Masunov, A.E.; Hagan, D.J.; Van Stryland, E.W. Electronic Nature of Neutral and Charged Two-Photon Absorbing Squaraines for Fluorescence Bioimaging Application. ACS Omega 2019, 4, 14669–14679. [Google Scholar] [CrossRef] [PubMed]
- Karpenko, I.A.; Klymchenko, A.S.; Gioria, S.; Kreder, R.; Shulov, I.; Villa, P.; Mely, Y.; Hiberta, M.; Bonnet, D. Squaraine as a bright, stable and environment sensitive far-red label for receptor-specific cellular imaging. Chem. Commun. 2015, 51, 2960–2963. [Google Scholar] [CrossRef] [Green Version]
- Liu, W.; McGarraugh, H.H.; Smith, B.D. Fluorescent Thienothiophene-Containing Squaraine Dyes and Threaded Supramolecular Complexes with Tunable Wavelengths between 600–800 nm. Molecules 2018, 23, 2229. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Martins, T.D.; Lima, E.; Boto, R.E.; Ferreira, D.; Fernandes, J.R.; Almeida, P.; Ferreira, L.F.V.; Silva, A.M.; Reis, L.V. Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects. Materials 2020, 13, 2083. [Google Scholar] [CrossRef]
- Hanming, D.; Qing, S.; Jinjun, S.; Wenjiung, W.; Fan, G.; Xiaochen, D. Small molecular NIR-II fluorophores for cancer phototheranostics. Innovation 2021, 2, 100082. [Google Scholar] [CrossRef]
- Zhang, W.; Deng, W.; Zhang, H.; Sun, X.; Huang, T.; Wang, W.; Sun, P.; Fan, Q.; Huang, W. Bioorthogonal-targeted 1064 nm excitation theranostic nanoplatform for precise NIR-IIa fluorescence imaging guided efficient NIR-II photothermal therapy. Biomaterials 2020, 243, 119934. [Google Scholar] [CrossRef] [PubMed]
- Büschel, M.; Ajayaghosh, A.; Arunkumar, E.; Daub, J. Redox-Switchable Squaraines with Extended Conjugation. Org. Lett. 2003, 5, 2975–2978. [Google Scholar] [CrossRef] [PubMed]
- Chen, J.; Winter, R.F. Studies on a Vinyl Ruthenium-Modified Squaraine Dye: Multiple Visible/Near-Infrared Absorbance Switching through Dye- and Substituent-Based Redox Processes. Chem. Eur. J. 2012, 18, 10733–10741. [Google Scholar] [CrossRef]
- Maltese, V.; Cospito, S.; Beneduci, A.; De Simone, B.C.; Russo, N.; Chidichimo, G.; Janssen, R.A.J. Electro-optical Properties of Neutral and Radical Ion Thienosquaraines. Chem. Eur. J. 2016, 22, 10179–10186. [Google Scholar] [CrossRef] [PubMed]
- You, L.-X.; Wang, L.; Zhang, L.; Jiang, X.-X.; Qin, S.-F.; Rensing, C.; Fu, N.-Y.; Sun, J.-J. Electro-oxidation of indole-based squaraine dye: A combined in-situ spectroelectrochemical and theoretical study. J. Electroanal. Chem. 2018, 827, 73–78. [Google Scholar] [CrossRef]
- Monk, P.M.S.; Mortimer, R.J.; Rosseinsky, D.R. Electrochromism and Electrochromic Devices; Cambridge University Press: Cambridge, UK, 2007. [Google Scholar]
- Mortimer, R.J. Electrochromic Materials. Annu. Rev. Mater. Res. 2011, 41, 241–268. [Google Scholar] [CrossRef]
- Mortimer, R.J.; Rosseinsky, D.R.; Monk, P.M.S. Electrochromic Materials and Devices; Wiley-VCH: Weinheim, Germany, 2015; p. 211. [Google Scholar]
- Corrente, G.A.; Beneduci, A. Overview on the Recent Progress on Electrofluorochromic Materials and Devices: A Critical Synopsis. Adv. Opt. Mater. 2020, 8, 2000887. [Google Scholar] [CrossRef]
- Paternò, G.M.; Barbero, N.; Galliano, S.; Barolo, C.; Lanzani, G.; Scotognella, F.; Borrelli, R. Excited state photophysics of squaraine dyes for photovoltaic applications: An alternative deactivation scenario. J. Mater. Chem. C 2018, 6, 2778–2785. [Google Scholar] [CrossRef] [Green Version]
- Sun, P.; Wu, Q.; Sun, X.; Miao, H.; Deng, W.; Zhang, W.; Fan, Q.; Huang, W. J-Aggregate squaraine nanoparticles with bright NIR-II fluorescence for imaging guided photothermal therapy. Chem. Commun. 2018, 54, 13395–13398. [Google Scholar] [CrossRef]
- Chaudhuri, S.; Verderame, M.; Mako, T.L.; Nuwan Bandara, Y.M.D.Y.; Fernando, A.I.; Levine, M. Synthetic β-Cyclodextrin Dimers for Squaraine Binding: Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity. Eur. J. Org. Chem. 2018, 17, 1964–1974. [Google Scholar] [CrossRef] [Green Version]
- Bricks, J.L.; Slominskii, Y.L.; Panas, I.D.; Demchenko, A.P. Fluorescent J-aggregates of cyanine dyes: Basic research and applications review. Methods Appl. Fluoresc. 2017, 6, 012001. [Google Scholar] [CrossRef] [Green Version]
- Shen, C.A.; Würthner, F. NIR-emitting squaraine J-aggregate nanosheets. Chem. Commun. 2020, 56, 9878–9881. [Google Scholar] [CrossRef]
- Shimizu, M.; Hiyama, T. Organic Fluorophores Exhibiting Highly Efficient Photoluminescence in the Solid State. Chem. Asian J. 2010, 5, 1516–1531. [Google Scholar] [CrossRef]
- Yang, Q.; Yang, D.; Zhao, S.; Huang, Y.; Xu, Z.; Liu, X.; Gong, W.; Fan, X.; Huang, Q.; Xu, X. The improved performance of solution-processed SQ:PC71BM photovoltaic devices via MoO3 as the anode modification layer. Appl. Surf. Sci. 2013, 284, 849–854. [Google Scholar] [CrossRef] [Green Version]
- Beneduci, A.; Cospito, S.; La Deda, M.; Chidichimo, G. Highly fluorescent thienoviologen-based polymer gels for single layer electrofluorochromic devices. Adv. Funct. Mater. 2015, 25, 1240–1247. [Google Scholar] [CrossRef]
- Tian, M.; Furuki, M.; Iwasa, I.; Sato, Y.; Pu, L.S.; Tatsuura, S. Search for Squaraine Derivatives That Can Be Sublimed without Thermal Decomposition. J. Phys. Chem. B 2002, 106, 4370–4376. [Google Scholar] [CrossRef]
- Peck, E.M.; Liu, W.; Spence, G.T.; Shaw, S.K.; Davis, A.P.; Destecroix, H.; Smith, B.D. Rapid Macrocycle Threading by a Fluorescent Dye–Polymer Conjugate in Water with Nanomolar Affinity. J. Am. Chem. Soc. 2015, 137, 8668–8671. [Google Scholar] [CrossRef] [Green Version]
- Chidichimo, G.; De Simone, B.C.; Imbardelli, D.; De Benedittis, M.; Barberio, M.; Ricciardi, L.; Beneduci, A. Influence of Oxygen Impurities on the Electrochromic Response of Viologen-Based Plastic Films. J. Phys. Chem. C 2014, 118, 13484–13492. [Google Scholar] [CrossRef]
Compound | a Eg | a Eox | a Ered | b ΔE |
---|---|---|---|---|
(eV) | (V) | |||
DIBSQ | 1.66 | 0.46 | −1.20 | 0.50 |
TSQ1 | 1.16 | −0.12 | −1.28 | 0.65 |
TSQ2 | 0.95 | −0.05 | −1.00 | 0.60 |
A%peak1 (nm) | A%peak2 (nm) | A%peak3 (nm) | R2 | Χ2 | ||
---|---|---|---|---|---|---|
Aggregates I | Aggregates II | Monomer | ||||
TSQ1 | 0.0 V | 58 (566) | 16 (632) | 26 (681) | 0.9995 | 4.4 × 10−5 |
0.75 V | 16 (536) | 38 (590) | 46 (654) | 0.9997 | 2.2 × 10−5 | |
1.0 V | 16 (531) | 6 (577) | 78 (631) | 0.9963 | 6.5 × 10−5 | |
1.5 V | 29 (533) | 6 (580) | 65 (647) | 0.9944 | 3.4 × 10−5 | |
TSQ2 | 0.0 V | 29 (557) | 71 (605) | 0.9973 | 3.2 × 10−4 | |
0.75 V | 28 (557) | 72 (604) | 0.9972 | 28 × 10−4 | ||
1.5 V | 40 (549) | 39 (602) | 21 (664) | 0.9971 | 7.0 × 10−5 | |
1.75 V | 44 (549) | 33 (603) | 23 (662) | 0.9955 | 54 × 10−5 |
Pulse Sequence V1_V2(V) - T1_t2 (s) | ||||
---|---|---|---|---|
DIBSQ/Fc | -2_2–60_60 | 1.52 (0.07) | 58 (1) | 22 (2) |
2_-2–60_60 | 1.8 (0.1) | 59 (1) | 17 (2) | |
TSQ1/EV | 2_-2–60_60 | 3 (0.2) | 47 (2) | 20 (2) |
TSQ2/EV | 2_-2–40_60 | 1.55 (0.04) | 32 (1) | 49 (1) |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Corrente, G.A.; Parisi, F.; Maltese, V.; Cospito, S.; Imbardelli, D.; La Deda, M.; Beneduci, A. Panchromatic Fluorescence Emission from Thienosquaraines Dyes: White Light Electrofluorochromic Devices. Molecules 2021, 26, 6818. https://doi.org/10.3390/molecules26226818
Corrente GA, Parisi F, Maltese V, Cospito S, Imbardelli D, La Deda M, Beneduci A. Panchromatic Fluorescence Emission from Thienosquaraines Dyes: White Light Electrofluorochromic Devices. Molecules. 2021; 26(22):6818. https://doi.org/10.3390/molecules26226818
Chicago/Turabian StyleCorrente, Giuseppina Anna, Francesco Parisi, Vito Maltese, Sante Cospito, Daniela Imbardelli, Massimo La Deda, and Amerigo Beneduci. 2021. "Panchromatic Fluorescence Emission from Thienosquaraines Dyes: White Light Electrofluorochromic Devices" Molecules 26, no. 22: 6818. https://doi.org/10.3390/molecules26226818