Triphenylamine, Carbazole or Tetraphenylethylene-Functionalized Benzothiadiazole Derivatives: Aggregation-Induced Emission (AIE), Solvatochromic and Different Mechanoresponsive Fluorescence Characteristics
Abstract
:1. Introduction
2. Results and Discussion
2.1. Aggregation-Inducing Characteristics of Compounds 1–3
2.2. Solvatochromic Effect of Compounds 1–3
2.3. Solid-State Fluorescence Characteristics of Compounds 1–3
3. Materials and Methods
3.1. General Methods
3.2. General Synthetic Procedure of Intermediate I
3.3. General Synthetic Procedure and Characterization of Dibenzobenzimidazole Derivatives 1–3
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
- Chi, Z.-G.; Zhang, X.-Q.; Xu, B.-J.; Zhou, X.; Ma, C.-P.; Zhang, Y.; Liu, S.-W.; Xu, J.-R. Recent advances in organic mechanofluorochromic materials. Chem. Soc. Rev. 2012, 41, 3878–3896. [Google Scholar] [CrossRef] [PubMed]
- Sagara, Y.; Kato, T. Mechanically induced luminescence changes in molecular assemblies. Nat. Chem. 2009, 1, 605–610. [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, 1073–1095. [Google Scholar] [CrossRef] [PubMed]
- Ciardelli, F.; Giacomo Ruggeri, G.; Pucci, A. Dye-containing polymers: Methods for preparation of mechanochromic materials. Chem. Soc. Rev. 2013, 42, 857–870. [Google Scholar] [CrossRef] [PubMed]
- Yin, Y.; Chen, Z.; Run-Hao Li, R.-H.; Yi, F.; Liang, X.-C.; Cheng, S.-Q.; Wang, K.; Sun, Y.; Liu, Y. Highly Emissive Multipurpose Organoplatinum (II) Metallacycles with Contrasting Mechanoresponsive Features. Inorg. Chem. 2022, 61, 2883–2891. [Google Scholar] [CrossRef] [PubMed]
- Chen, Z.; Li, Z.; Hu, F.; Yu, G.-A.; Yin, J.; Liu, S.-H. Novel carbazole-based aggregation-induced emission-active gold (I) complexes with various mechanofluorochromic behaviors. Dye. Pigment. 2016, 125, 169–178. [Google Scholar] [CrossRef]
- Chen, Z.; Liang, J.-H.; Nie, Y.-T.; Xu, X.; Yu, G.-A.; Yin, J.; Liu, S.-H. A novel carbazole-based gold (I) complex with interesting solid-state, multistimuli-responsive characteristics. Dalton Trans. 2015, 44, 17473. [Google Scholar] [CrossRef]
- Zhu, Y.-X.; Wei, Z.-W.; Pan, M.; Wang, H.-P.; Zhang, J.-Y.; Su, C.-Y. A new TPE-based tetrapodal ligand and its Ln (III) complexes: Multi-stimuli responsive AIE (aggregation-induced emission)/ILCT (intraligand charge transfer)-bifunctional photoluminescence and NIR emission sensitization. Dalton Trans. 2016, 45, 943–950. [Google Scholar] [CrossRef]
- Roy, B.; Reddy, M.-C.; Hazra, P. Developing the structure–property relationship to design solid state multi-stimuli responsive materials and their potential applications in different fields. Chem. Sci. 2018, 9, 3592. [Google Scholar] [CrossRef] [Green Version]
- Davis, D.; Hamilton, A.; Yang, J. Force-induced activation of covalent bonds in mechanoresponsive polymeric materials. Nature 2009, 459, 6872. [Google Scholar] [CrossRef]
- Chen, Z.; Wu, D.; Han, X.; Liang, J.-H.; Yin, J.; Yu, G.-A.; Liu, S.-H. A novel fluorene-based gold (I) complex with aggregate fluorescence change: A single-component white light-emitting luminophore. Chem. Commun. 2014, 50, 11033. [Google Scholar] [CrossRef] [PubMed]
- Gao, Y.; Zhang, Y.; Baoxing Xu, B.-X. Confined Water-Assistant Thermal Response of a Graphene Oxide Heterostructure and Its Enabled Mechanical Sensors for Load Sensing and Mode Differentiation. ACS Appl. Mater. Interfaces 2019, 11, 19596–19604. [Google Scholar] [CrossRef] [PubMed]
- Inci, E.; Topcu, G.; Guner, T.; Demirkurt, M.; Demir, M.-M. Recent developments of colorimetric mechanical sensors based on polymer composites. J. Mater. Chem. C 2020, 8, 12036–12053. [Google Scholar] [CrossRef]
- Sarma, M.; Chen, L.-M.; Chen, Y.-S.; Ken-Tsung Wong, K.-Y. Exciplexes in OLEDs: Principles and promises. Mater. Sci. Eng. R Rep. 2022, 150, 100689. [Google Scholar] [CrossRef]
- Zeng, J.-J.; Guo, J.-J.; Liu, H.; Zhao, Z.-J.; Tang, B.-Z. A Multifunctional Bipolar Luminogen with Delayed Fluorescence for High-Performance Monochromatic and Color-Stable Warm-White OLEDs. Adv. Funct. Mater. 2020, 30, 2000019. [Google Scholar] [CrossRef]
- Wu, C.-J.; Miao, J.-S.; Wang, L.; Zhang, Y.-M.; Li, K.; Zhu, W.-G.; Yang, C.-L. Red and near-infrared emissive palladium (II) complexes with tetradentate coordination framework and their application in OLEDs. Chem. Eng. J. 2022, 446, 136834. [Google Scholar] [CrossRef]
- Zhao, H.-P.; Cun, Y.-K.; Bai, X.; Xiao, D.-W.; Qiu, J.-B.; Song, Z.-G.; Liao, J.-Y.; Yang, Z.-W. Entirely Reversible Photochromic Glass with High Coloration and Luminescence Contrast for 3D Optical Storage. ACS Energy Lett. 2022, 7, 2060–2069. [Google Scholar] [CrossRef]
- Lin, S.-S.; Lin, H.; Huang, Q.-M.; Cheng, Y.; Xu, J.; Wang, J.-M.; Xiang, X.-Q.; Wang, C.-Y.; Zhang, L.-Q.; Wang, Y.-S. A Photostimulated BaSi2O5: Eu2+,Nd3+ Phosphor-in-Glass for Erasable-Rewritable Optical Storage Medium. Laser Photonics Rev. 2019, 13, 1900006. [Google Scholar] [CrossRef]
- Franken, L.-E.; Wei, Y.-C.; Chen, J.-W.; Boekema, E.-J.; Zhao, D.; Stuart, M.-C.; Feringa, B.-L. Solvent Mixing to Induce Molecular Motor Aggregation into Bowl-Shaped Particles: Underlying Mechanism, Particle Nature, and Application to Control Motor Behavior. J. Am. Chem. Soc. 2018, 140, 7860–7868. [Google Scholar] [CrossRef]
- Qiu, S.; Zhang, Z.; Wu, Y.; Tong, F.; Chen, K.; Liu, G.; Lei Zhang, L.; Wang, Z.; Qu, D.-H.; Tian, T. Vibratile Dihydrophenazines with Controllable Luminescence Enabled by Precise Regulation of π-Conjugated Wings. CCS Chem. 2021, 3, 2239–2248. [Google Scholar] [CrossRef]
- Yang, S.; Zhao, C.-X.; Crespi, S.; Li, X.; Zhang, Q.; Zhang, Z.-Y.; Ju Mei, J.; Tian, H.; Qu, D.-H. Reversibly modulating a conformation-adaptive fluorophore in [2] catenane. Chem 2021, 7, 1544–1556. [Google Scholar] [CrossRef]
- Zong, Z.; Qi Zhang, Q.; Qiu, S.-H.; Wang, Q.; Zhao, C.; Zhao, C.-X.; Tian, H.; Qu, D.-H. Dynamic Timing Control over Multicolor Molecular Emission by Temporal Chemical Locking. Angew. Chem. Int. Ed. 2022, 61, e202116414. [Google Scholar] [CrossRef] [PubMed]
- Wang, Q.; Zhang, Q.; Zhang, Q.-W.; Li, X.; Zhao, C.-X.; Xu, T.-Y.; Qu, D.-H.; Tian, H. Color-tunable single-fluorophore supramolecular system with assembly-encoded emission. Nat. Commun. 2020, 11, 158. [Google Scholar] [CrossRef] [PubMed]
- Tang, W.; Zuo, C.-D.; Ma, C.-Y.; Wang, Y.-Z.; Li, Y.-K.; Yuan, X.-X.; Wang, E.; Wen, Z.-C.; Cao, Y.-G. Designing photochromic materials with high photochromic contrast and large luminescence modulation for hand-rewritable information displays and dual-mode optical storage. Chem. Eng. J. 2022, 435, 134670. [Google Scholar] [CrossRef]
- Usui, R.; Yamamoto, K.; Okajima, H.; Mutoh, K.; Sakamoto, A.; Abe, J.; Kobayashi, Y. Photochromic Radical Complexes That Show Heterolytic Bond Dissociation. J. Am. Chem. Soc. 2020, 142, 10132–10142. [Google Scholar] [CrossRef]
- Bessinger, D.; Muggli, K.; Beetz, M.; Auras, F.; Bein, T. Fast-Switching Vis-IR Electrochromic Covalent Organic Frameworks. J. Am. Chem. Soc. 2021, 143, 7351–7357. [Google Scholar] [CrossRef]
- Zhang, W.; Li, H.-Z.; Elezzabi, A.-Y. Electrochromic Displays Having Two-Dimensional CIE Color Space Tunability. Adv. Funct. Mater. 2022, 32, 2108341. [Google Scholar] [CrossRef]
- Chang, T.-C.; Cao, X.; Long, Y.; Luo, H.-J.; Jin, P. How to properly evaluate and compare the thermochromic performance of VO2- based smart coatings. J. Mater. Chem. A 2019, 7, 24164–24172. [Google Scholar] [CrossRef]
- Kim, D.-H.; Bae, J.; Lee, J.; Ahn, J.; Hwang, W.-T.; Ko, J.; Kim, D. Porous Nanofiber Membrane: Rational Platform for Highly Sensitive Thermochromic Sensor. Adv. Funct. Mater. 2022, 32, 2200463. [Google Scholar] [CrossRef]
- Yin, Y.; Chen, Z.; Li, R.-H.; Yuan, C.; Shao, T.-Y.; Wang, K.; Tan, H.-W.; Sun, Y. Ligand-Triggered Platinum (II) Metallacycle with Mechanochromic and Vapochromic Responses. Inorg. Chem. 2021, 60, 9387–9393. [Google Scholar] [CrossRef]
- Cheng, S.-Q.; Chen, Z.; Yin, Y.; Sun, Y.; Liu, S.-H. Progress in mechanochromic luminescence of gold (I) complexes. Chin. Chem. Lett. 2021, 32, 3718–3732. [Google Scholar] [CrossRef]
- Yin, Y.; Hu, H.; Chen, Z.; Liu, H.-L.; Fan, C.-B.; Pu, S.-Z. Tetraphenylethene or triphenylethylene-based luminophors: Tunable aggregation-induced emission (AIE), solid-state fluorescence and mechanofluorochromic characteristics. Dye. Pigment. 2021, 184, 108828. [Google Scholar] [CrossRef]
- Wang, Y.-Y.; Shen, R.-P.; Wang, S.; Zhang, Y.-M.; Zhang, S.-X. Dynamic Metal–Ligand Interaction of Synergistic Polymers for Bistable See-Through Electrochromic Devices. Adv. Mater. 2022, 34, 2104413. [Google Scholar] [CrossRef] [PubMed]
- Huang, Y.; Yang, C.; Deng, B.-H.; Wang, C.; Li, Q.-W.; Thibault, C.; Huang, K.; Huo, K.; Wu, H. Nanostructured pseudocapacitors with pH-tunable electrolyte for electrochromic smart windows. Nano Energy 2019, 66, 104200. [Google Scholar] [CrossRef]
- Zhang, Q.; Tsai, C.-Y.; Li, L.-J.; Liaw, D.-J. Colorless-to-colorful switching electrochromic polyimides with very high contrast ratio. Nat. Commun. 2019, 10, 1239. [Google Scholar] [CrossRef] [PubMed]
- Pucci, A.; Ruggeriac, G. Mechanochromic polymer blends. J. Mater. Chem. 2011, 21, 8282–8291. [Google Scholar] [CrossRef]
- Ariga, K.; Mori, T.; Hill, J.-P. Mechanical Control of Nanomaterials and Nanosystems. Adv. Mater. 2012, 24, 158. [Google Scholar] [CrossRef]
- Zhang, X.-Q.; Chi, Z.-G.; Zhang, Y.; Liu, S.-W.; Xu, J.-R. Recent advances in mechanochromic luminescent metal complexes. J. Mater. Chem. C 2013, 1, 3376–3390. [Google Scholar] [CrossRef]
- Louis, M.; Sethy, R.; Kumar, J.; Katao, S.; Guillot, R.; Nakashima, T.; Allain, C.; Kawai, T.; Métivier, R. Mechano-responsive circularly polarized luminescence of organic solid-state chiral emitters. Chem. Sci. 2019, 10, 843–847. [Google Scholar] [CrossRef] [Green Version]
- Conesa-Egea, J.; Nogal, N.; Martínez, J.-I.; Fernández-Moreira, V.; Rodríguez-Mendoza, U.-R.; González-Platas, J. Smart composite films of nanometric thickness based on copper–iodine coordination polymers. Toward sensors. Chem. Sci. 2018, 9, 8000–8010. [Google Scholar] [CrossRef] [Green Version]
- Luo, J.-D.; Xie, Z.-L.; Lam, J.-W.-Y.; Cheng, L.; Chen, H.-Y.; Qiu, C.-F.; Kwok, H.-S.; Zhan, X.-W.; Liu, Y.-Q.; Zhu, D.-B.; et al. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun. 2001, 18, 1740–1741. [Google Scholar] [CrossRef] [PubMed]
- An, B.-K.; Kwon, S.-K.; Jung, S.-D.; Park, S.-Y. Enhanced emission and its switching in fluorescent organic nanoparticles. J. Am. Chem. Soc. 2002, 124, 14410–14415. [Google Scholar] [CrossRef] [PubMed]
- Luo, Z.-T.; Yuan, X.; Yu, Y.; Zhang, Q.-B.; Leong, D.-T.; Lee, J.-Y.; Xie, J.-P. From Aggregation-Induced Emission of Au (I)—Thiolate Complexes to Ultrabright Au (0) @ Au (I)—Thiolate Core—Shell Nanoclusters. J. Am. Chem. Soc. 2012, 134, 16662. [Google Scholar] [CrossRef] [PubMed]
- Goswami, N.; Yao, Q.; Luo, Z.; Li, J.; Chen, T.; Xie, J. Luminescent Metal Nanoclusters with Aggregation-Induced Emission. J. Phys. Chem. Lett. 2016, 7, 962. [Google Scholar] [CrossRef]
- Kang, X.; Wang, S.; Song, Y.; Jin, S.; Sun, G.; Yu, H.; Zhu, M. Bimetallic Au2Cu6 Nanoclusters: Strong Luminescence Induced by the Aggregation of Copper (I) Complexes with Gold (0) Species. Angew. Chem. Int. Ed. 2016, 55, 3611. [Google Scholar] [CrossRef]
- Liu, C.-C.; Wang, X.-X.; Liu, J.-K.; Yue, Q.; Chen, S.-J.; Lam, J.W.-Y.; Luo, L.; Tang, B.-Z. Near-Infrared AIE Dots with Chemiluminescence for Deep-Tissue Imaging. Adv. Mater. 2020, 32, 2004685. [Google Scholar] [CrossRef]
- Zhang, N.; Gao, H.; Jia, Y.-L.; Pan, J.-B.; Luo, X.-L.; Chen, H.-Y.; Xu, J.-J. Ultrasensitive Nucleic Acid Assay Based on AIE-Active Polymer Dots with Excellent Electrochemiluminescence Stability. Anal. Chem. 2021, 93, 6857–6864. [Google Scholar] [CrossRef]
- Liu, F.-T.; Tan, Y.-B.; Liu, H.; Tang, X.-Y.; Gao, L.; Du, C.-Y.; Min, J.-R.; Jin, H.-X.; Lu, P. High-efficiency near-infrared fluorescent organic light-emitting diodes with small efficiency roll-off based on AIE-active phenanthrol [9, 10-d] imidazole derivatives. J. Mater. Chem. C 2020, 8, 6883–6890. [Google Scholar] [CrossRef]
- Yuan, Y.; Chen, J.-X.; Lu, F.; Tong, Q.-X.; Yang, Q.-D.; Mo, H.-W.; Ng, T.-W.; Wong, F.-L.; Guo, Z.-Q.; Ye, J.; et al. Bipolar Phenanthroimidazole Derivatives Containing Bulky Polyaromatic Hydrocarbons for Nondoped Blue Electroluminescence Devices with High Efficiency and Low Efficiency Roll-Off. Chem. Mater. 2013, 25, 4957–4965. [Google Scholar] [CrossRef]
- Chen, W.-C.; Yuan, Y.; Wu, G.-F.; Wei, H.-X.; Tang, L.; Tong, Q.-X.; Wong, F.-L.; Lee, C.-S. Staggered Face-to-Face Molecular Stacking as a Strategy for Designing Deep-Blue Electroluminescent Materials with High Carrier Mobility. Adv. Opt. Mater. 2014, 2, 626–631. [Google Scholar] [CrossRef]
- Wang, k.; Wang, S.-P.; Wei, J.-B.; Miao, Y.; Liu, Y.; Wang, Y. Novel diarylborane-phenanthroimidazole hybrid bipolar host materials for high-performance red, yellow and green electrophosphorescent devices. Org. Electron. 2014, 15, 3211. [Google Scholar] [CrossRef]
- Ekbote, A.; Han, S.-h.; Jadhav, T.; Mobin, S.-M.; Lee, J.-Y.; Misra, R. Stimuli responsive AIE active positional isomers of phenanthroimidazole as non-doped emitters in OLEDs. J. Mater. Chem. C 2018, 6, 2077–2087. [Google Scholar] [CrossRef]
- Liu, D.; Wei, J.-Y.; Tian, W.-W.; Jiang, W.; Sun, Y.-M.; Zhao, Z.; Tang, B.-Z. Endowing TADF luminophors with AIE properties through adjusting flexible dendrons for highly efficient solution-processed nondoped OLEDs. Chem. Sci. 2020, 11, 7194–7203. [Google Scholar] [CrossRef] [PubMed]
- Leung, C.-W.; Hong, Y.; Chen, S.; Zhao, E.; Lam, J.-W. A Photostable AIE Luminogen for Specific Mitochondrial Imaging and Tracking. J. Am. Chem. Soc. 2013, 135, 62–65. [Google Scholar] [CrossRef] [PubMed]
- Wang, D.; Su, H.; Kwok, R.; Hu, X.-L.; Zou, H.; Lee, M.M.; Xu, W.; Lam, J.-W.; Tang, B.-Z. Rational design of a water-soluble NIR AIEgen, and its application in ultrafast wash-free cellular imaging and photodynamic cancer cell ablation. Chem. Sci. 2018, 9, 3685–3693. [Google Scholar] [CrossRef] [Green Version]
- Yu, T.; Ou, D.; Yang, Z.; Huang, Q.; Mao, Z.; Chen, J.; Zhang, Y.; Liu, S.; Xu, J.; Bryce, M.-R.; et al. The HOF structures of The HOF structures of nitrotetraphenylethene derivatives provide new insights into the nature of AIE and a way to design mechanoluminescent materials. Chem. Sci. 2017, 8, 1163–1168. [Google Scholar] [CrossRef] [Green Version]
- Tang, A.-L.; Yin, Y.; Chen, Z.; Fan, C.-B.; Liu, G.; Pu, S.-Z. A multifunctional aggregation-induced emission (AIE)-active fluorescent chemosensor for detection of Zn2+ and Hg2+. Tetrahedron 2019, 75, 130489. [Google Scholar] [CrossRef]
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2022 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
Yang, Y.; Deng, D.; Deng, X.; Chen, Z.; Pu, S. Triphenylamine, Carbazole or Tetraphenylethylene-Functionalized Benzothiadiazole Derivatives: Aggregation-Induced Emission (AIE), Solvatochromic and Different Mechanoresponsive Fluorescence Characteristics. Molecules 2022, 27, 4740. https://doi.org/10.3390/molecules27154740
Yang Y, Deng D, Deng X, Chen Z, Pu S. Triphenylamine, Carbazole or Tetraphenylethylene-Functionalized Benzothiadiazole Derivatives: Aggregation-Induced Emission (AIE), Solvatochromic and Different Mechanoresponsive Fluorescence Characteristics. Molecules. 2022; 27(15):4740. https://doi.org/10.3390/molecules27154740
Chicago/Turabian StyleYang, Yue, Diandian Deng, Xiaowen Deng, Zhao Chen, and Shouzhi Pu. 2022. "Triphenylamine, Carbazole or Tetraphenylethylene-Functionalized Benzothiadiazole Derivatives: Aggregation-Induced Emission (AIE), Solvatochromic and Different Mechanoresponsive Fluorescence Characteristics" Molecules 27, no. 15: 4740. https://doi.org/10.3390/molecules27154740