ICT and AIE Characteristics Two Cyano-Functionalized Probes and Their Photophysical Properties, DFT Calculations, Cytotoxicity, and Cell Imaging Applications
Abstract
:1. Introduction
2. Results and Discussion
2.1. Electronic Feature of AIE-1 and AIE-2 by Density Functional Theory (DFT) Calculation
2.2. Aggregation Study by UV-Vis and Fluorescence Spectroscopy
2.3. Aggregation Confirmed by Scanning Electron Microscope (SEM) and Dynamic Light Scattering (DLS) Studies
2.4. Emission of AIE-1 and AIE-2 in Different Solvents and in Different Concentrations:
2.5. Cytotoxicity and Cell Imaging Applications of AIE-1 and AIE-2:
3. Experimental Section
3.1. Details of General Instruments and Materials
3.2. Synthesis and Characterization
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Du, J.; Hu, M.; Fan, J.; Peng, X. Fluorescent chemodosimeters using “mild” chemical events for the detection of small anions and cations in biological and environmental media. Chem. Soc. Rev. 2012, 41, 4511–4535. [Google Scholar] [CrossRef] [PubMed]
- Huang, J.; Sun, N.; Yang, J.; Tang, R.; Li, Q.; Ma, D.; Qin, J.; Li, Z. Benzene-cored fluorophors with TPE peripheries: facile synthesis, crystallization-induced blue-shifted emission, and efficient blue luminogens for non-doped OLEDs. J. Mater. Chem. 2012, 22, 12001–12007. [Google Scholar] [CrossRef]
- Liu, C.; Wang, K.; Gong, X.; Heeger, A.J. Low bandgap semiconducting polymers for polymeric photovoltaics. Chem. Soc. Rev. 2016, 45, 4825–4846. [Google Scholar] [CrossRef] [PubMed]
- Chen, Z.; Zheng, Y.; Yan, H.; Facchetti, A. Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transistors. J. Am. Chem. Soc. 2009, 131, 8–9. [Google Scholar] [CrossRef] [PubMed]
- Han, T.; Feng, X.; Chen, D.; Dong, Y. A diethylaminophenol functionalized Schiff base: crystallization-induced emission-enhancement, switchable fluorescence and application for security printing and data storage. J. Mater. Chem. C 2015, 3, 7446–7454. [Google Scholar] [CrossRef]
- Wang, M.; Zhang, D.; Zhang, G.; Zhu, D. The convenient fluorescence turn-on detection of heparin with a silole derivative featuring an ammonium group. Chem. Commun. 2008, 37, 4469–4471. [Google Scholar] [CrossRef] [PubMed]
- Qin, W.; Alifu, N.; Cai, Y.; Lam, J.W.Y.; He, X.; Su, H.; Zhang, P.; Qian, J.; Tang, B.Z. Synthesis of an efficient far-red/near-infrared luminogen with AIE characteristics for in vivo bioimaging applications. Chem. Commun. 2019, 55, 5615–5618. [Google Scholar] [CrossRef] [PubMed]
- Samanta, S.; He, Y.; Sharma, A.; Kim, J.; Pan, W.; Yang, Z.; Li, J.; Yan, W.; Liu, L.; Qu, J.; et al. Fluorescent Probes for Nanoscopic Imaging of Mitochondria. Chem 2019, 5, 1697–1726. [Google Scholar] [CrossRef]
- Samanta, S.; Gong, W.; Li, W.; Sharma, A.; Shim, I.; Zhang, W.; Das, P.; Pan, W.; Liu, L.; Yang, Z.; et al. Organic fluorescent probes for stochastic optical reconstruction microscopy (STORM): Recent highlights and future possibilities. Coord. Chem. Rev. 2019, 380, 17–34. [Google Scholar] [CrossRef]
- Luo, J.; Xie, Z.; Lam, J.W.Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H.S.; Zhan, X.; Liu, Y.; Zhu, D.; et al. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun. 2001, 18, 1740–1741. [Google Scholar] [CrossRef]
- Mei, J.; Leung, N.L.C.; Kwok, R.T.K.; Lam, J.W.Y.; Tang, B.Z. Aggregation-induced emission: together we shine, united we soar! Chem. Rev. 2015, 115, 11718–11940. [Google Scholar] [CrossRef]
- Chen, S.; Wang, H.; Hong, Y.; Tang, B.Z. Fabrication of fluorescent nanoparticles based on AIE luminogens (AIE dots) and their applications in bioimaging. Mater. Horiz. 2016, 3, 283–293. [Google Scholar] [CrossRef]
- Hu, R.; Leung, L.C.N.; Tang, B.Z. AIE macromolecules: syntheses, structures and functionalities. Chem. Soc. Rev. 2014, 43, 4494–4562. [Google Scholar] [CrossRef] [PubMed]
- Chang, Z.; Jiang, Y.; He, B.; Chen, J.; Yang, Z.; Lu, P.; Kwok, H.S.; Zhao, Z.; Qiu, H.; Tang, B.Z. Aggregation-enhanced emission and efficient electroluminescence of tetraphenylethene-cored luminogens. Chem. Commun. 2013, 49, 594–596. [Google Scholar] [CrossRef] [PubMed]
- Hong, Y.; Lam, J.W.Y.; Tang, B.Z. Aggregation-induced emission. Chem. Soc. Rev. 2011, 40, 5361–5388. [Google Scholar] [CrossRef] [Green Version]
- Li, H.; Chi, Z.; Xu, B.; Zhang, X.; Li, X.; Liu, S.; Zhang, Y.; Xu, J. Aggregation-induced emission enhancement compounds containing triphenylamine-anthrylenevinylene and tetraphenylethene moieties. J. Mater. Chem. 2011, 21, 3760–3767. [Google Scholar] [CrossRef]
- Zhang, X.; Chi, Z.; Zhou, X.; Liu, S.; Zhang, Y.; Xu, J. Influence of Carbazolyl Groups on Properties of Piezofluorochromic Aggregation-Enhanced Emission Compounds Containing Distyrylanthracene. J. Phys. Chem. C 2012, 116, 23629–23638. [Google Scholar] [CrossRef]
- Hong, Y.; Lam, W.Y.J.; Tang, B.Z. Aggregation-induced emission: Phenomenon, mechanism and applications. Chem. Commun. 2009, 4332–4353. [Google Scholar] [CrossRef]
- Hu, F.; Liu, B. Organelle-specific bioprobes based on fluorogens with aggregation-induced emission (AIE) characteristics. Org. Biomol. Chem. 2016, 14, 9931–9944. [Google Scholar] [CrossRef] [Green Version]
- Meher, N.; Iyer, P.K. Pendant chain engineering to fine-tune the nanomorphologies and solid state luminescence of naphthalimide AIEEgens: Application to phenolic nitro-explosive detection in water. Nanoscale 2017, 9, 7674–7685. [Google Scholar] [CrossRef]
- Tarai, A.; Baruah, J.B. Changing π-Interactions and Conformational Adjustments of N-(Isonicotinylhydrazide)-1,8-naphthalimide by Hydration and Complexation Affect Photophysical Properties. Cryst. Growth Des. 2018, 18, 456–465. [Google Scholar] [CrossRef]
- Nie, H.; Chen, B.; Zeng, J.; Xiong, Y.; Zhao, Z.; Tang, B.Z. Excellent n-type light emitters based on AIE-active silole derivatives for efficient simplified organic light-emitting diodes. J. Mater. Chem. C 2018, 6, 3690–3698. [Google Scholar] [CrossRef]
- Meher, N.; Chowdhury, S.R.; Iyer, P.K. Aggregation induced emission enhancement and growth of naphthalimide nanoribbons via J-aggregation: insight into disaggregation induced unfolding and detection of ferritin at the nanomolar level. J. Mater. Chem. B 2016, 4, 6023–6031. [Google Scholar] [CrossRef]
- Meher, N.; Panda, S.; Kumar, S.; Iyer, P.K. Aldehyde group driven aggregation-induced enhanced emission in naphthalimides and its application for ultradetection of hydrazine on multiple platforms. Chem. Sci. 2018, 9, 3978–3985. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Mazumdar, P.; Maity, S.; Shyamal, M.; Das, D.; Sahoo, G.P.; Misra, A. Proton triggered emission and selective sensing of picric acid by the fluorescent aggregates of 6,7-dimethyl-2,3-bis-(2-pyridyl)-quinoxaline. Phys. Chem. Chem. Phys. 2016, 18, 7055–7067. [Google Scholar] [CrossRef] [PubMed]
- Li, X.; Jiang, M.; Lam, J.W.Y.; Tang, B.Z.; Qu, J.Y. Mitochondrial imaging with combined fluorescence and stimulated raman scattering microscopy using a probe of the aggregation-induced emission characteristic. J. Am. Chem. Soc. 2017, 139, 17022–17030. [Google Scholar] [CrossRef] [PubMed]
- Ni, F.; Zhu, Z.; Tong, X.; Xie, M.; Zhao, Q.; Zhong, C.; Zou, Y.; Yang, C. Organic emitter integrating aggregation-induced delayed fluorescence and room-temperature phosphorescence characteristics, and its application in time-resolved luminescence imaging. Chem. Sci. 2018, 9, 6150–6155. [Google Scholar] [CrossRef] [Green Version]
- Sasaki, S.; Drummen, G.P.C.; Konishi, G.-I. Recent advances in twisted intramolecular charge transfer (TICT) fluorescence and related phenomena in materials chemistry. J. Mater. Chem. C 2016, 4, 2731–2743. [Google Scholar] [CrossRef] [Green Version]
- Yang, Z.; Qin, W.; Lam, J.W.Y.; Chen, S.; Sung, H.H.Y.; Williams, I.D.; Tang, B.Z. Fluorescent pH sensor constructed from a heteroatom containing luminogen with tunable AIE and ICT characteristics. Chem. Sci. 2013, 4, 3725–3730. [Google Scholar] [CrossRef] [Green Version]
- Cao, C.; Liu, X.; Qiao, Q.; Zhao, M.; Yin, W.; Mao, D.; Zhang, H.; Xu, Z. A twisted-intramolecular-charge-transfer (TICT) based ratiometric fluorescent thermometer with a mega-Stokes shift and a positive temperature coefficient. Chem. Commun. 2014, 50, 15811–15814. [Google Scholar] [CrossRef]
- Zhao, J.; Chi, Z.; Zhang, Y.; Mao, Z.; Yang, Z.; Ubba, E.; Chi, Z. Recent progress in the mechanofluorochromism of cyanoethylene derivatives with aggregation-induced emission. J. Mater. Chem. C 2018, 6, 6327–6353. [Google Scholar] [CrossRef]
- Niu, G.; Zheng, X.; Zhao, Z.; Zhang, H.; Wang, J.; He, X.; Chen, Y.; Shi, X.; Ma, C.; Kwok, R.T.K.; et al. et al. Functionalized Acrylonitriles with Aggregation-Induced Emission: Structure Tuning by Simple Reaction-Condition Variation, Efficient Red Emission, and Two-Photon Bioimaging. J. Am. Chem. Soc. 2019, 141, 15111–15120. [Google Scholar] [CrossRef] [PubMed]
- Han, T.; Gu, X.; Lam, J.W.Y.; Leung, A.C.S.; Kwok, R.T.K.; Han, T.; Tong, B.; Shi, J.; Dong, Y.; Tang, B.Z. Diaminomaleonitrile-based Schiff bases: Aggregation-enhanced emission, red fluorescence, mechanochromism and bioimaging applications. J. Mater. Chem. C 2016, 4, 10430–10434. [Google Scholar] [CrossRef]
- Kumari, B.; Singh, S.P.; Santosh, R.; Dutta, A.; Mallajosyula, S.S.; Ghosal, S.; Kanvah, S. Branching effect on triphenylamine-CF3 cyanostilbenes: enhanced emission and aggregation in water. New J. Chem. 2019, 43, 4106–4115. [Google Scholar] [CrossRef]
- Sun, Q.K.; Liu, W.; Ying, S.A.; Wang, L.L.; Xue, S.F.; Yang, W.J. 9,10-Bis(N-alkylindole-3-yl-vinyl-2)anthracenes as a new series of alkyl length-dependent piezofluorochromic aggregation-induced emission homologues. RSC Adv. 2015, 5, 73046–73050. [Google Scholar] [CrossRef]
- Gabr, M.T.; Pigge, F.C. Rhenium tricarbonyl complexes of AIE active tetraarylethylene ligands: tuning luminescence properties and HSA-specific binding. Dalton Trans. 2017, 46, 15040–15047. [Google Scholar] [CrossRef]
- Mishra, R.K.; Vijayakumar, S.; Mal, A.; Karunakaran, V.; Janardhanan, J.C.; Maiti, K.K.; Praveen, V.K.; Ajayaghosh, A. Bimodal detection of carbon dioxide using fluorescent molecular aggregates. Chem. Commun. 2019, 55, 6046–6049. [Google Scholar] [CrossRef]
- Mandal, A.; Patel, B.K.; Shukla, R.; Chopra, D. Impact of the complementary electronic nature of C-X and M-X halogens and intramolecular X⋯O interaction on supramolecular assemblies of Zn (II) complexes of o-halophenyl substituted hydrazides. Cryst. Eng. Comm. 2017, 19, 1607–1619. [Google Scholar] [CrossRef]
- Zhang, R.; Gao, M.; Bai, S.; Liu, B. A fluorescent light-up platform with “AIE+ESIPT” characteristics for multi-target detection both in solution and on paper strip. J. Mater. Chem. B 2015, 3, 1590–1596. [Google Scholar] [CrossRef]
- Critchfield, F.E.; Gibson, J.A., Jr.; Hall, J.L. Dielectric Constant and Refractive Index from 20 to 35° and Density at 25° for the System Tetrahydrofuran-Water. J. Am. Chem. Soc. 1953, 75, 6044–6045. [Google Scholar] [CrossRef]
- Wang, Z.; Wang, M.; Peng, J.; Xie, Y.; Liu, M.; Gao, W.; Zhou, Y.; Huang, X.; Wu, H. Polymorphism and Multicolor Mechanofluorochromism of a D-π-A Asymmetric 4H-Pyran Derivative with Aggregation-Induced Emission Property. J. Phys. Chem. C 2019, 123, 27742–27751. [Google Scholar] [CrossRef]
- Yang, Z.; Chi, Z.; Yu, T.; Zhang, X.; Chen, M.; Xu, B.; Liu, S.; Zhang, Y.; Xu, J. Triphenylethylene carbazole derivatives as a new class of AIE materials with strong blue light emission and high glass transition temperature. J. Mater. Chem. 2009, 19, 5541–5546. [Google Scholar] [CrossRef]
- Tian, G.; Huang, W.; Cai, S.; Zhou, H.; Li, B.; Wang, Q.; Su, J. Small molecules based on diphenylamine and carbazole with large two-photon absorption cross sections and extraordinary AIEE properties. RSC Adv. 2014, 4, 38939–38942. [Google Scholar] [CrossRef]
- La, D.D.; Bhosale, S.V.; Jones, L.A.; Bhosale, S.V. Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications. ACS Appl. Mater. Interfaces 2018, 10, 12189–12216. [Google Scholar] [CrossRef]
- Peng, X.-L.; Ruiz-Barragan, S.; Li, Z.-S.; Li, Q.-S.; Blancafort, L. Restricted access to a conical intersection to explain aggregation induced emission in dimethyl tetraphenylsilole. J. Mater. Chem. C 2016, 4, 2802–2810. [Google Scholar] [CrossRef]
- Gopikrishna, P.; Meher, N.; Iyer, P.K. Functional 1,8-Naphthalimide AIE/AIEEgens: Recent Advances and Prospects. ACS Appl. Mater. Interfaces 2018, 10, 12081–12111. [Google Scholar] [CrossRef]
- Song, Q.; Wang, Y.; Hu, C.; Zhang, Y.; Sun, J.; Wang, K.; Zhang, C. Effect of stacking mode on the mechanofluorochromic properties of 3-aryl-2-cyano acrylamide derivatives. New J. Chem. 2015, 39, 659–663. [Google Scholar] [CrossRef]
- Zhang, Y.J.; Zhuang, G.L.; Ouyang, M.; Hu, B.; Song, Q.B.; Sun, J.W.; Zhang, C.; Gu, C.; Xu, Y.X.; Ma, Y.G. Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives. Dyes Pigm. 2013, 98, 486–492. [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]
- Upamali, K.A.N.; Estrada, L.A.; De, P.K.; Cai, X.; Krause, J.A.; Neckers, D.C. Carbazole-Based Cyano-Stilbene Highly Fluorescent Microcrystals. Langmuir, 2011, 27, 1573–1580. [Google Scholar] [CrossRef]
- Sun, J.W.; Dai, Y.Y.; Mi, O.Y.; Zhang, Y.J.; Zhan, L.L.; Zhang, C. Unique torsional cruciform π-architectures composed of donor and acceptor axes exhibiting mechanochromic and electrochromic properties. J. Mater. Chem. C 2015, 3, 3356–3363. [Google Scholar] [CrossRef]
- Zhao, Q.; Sun, J.Z. Red and near infrared emission materials with AIE characteristics. J. Mater. Chem. C 2016, 4, 10588–10609. [Google Scholar] [CrossRef]
- Xu, Y.; Wang, K.; Zhang, Y.; Xie, Z.; Zou, B.; Ma, Y. Fluorescence mutation and structural evolution of a π-conjugated molecular crystal during phase transition. J. Mater. Chem. C 2016, 4, 1257–1262. [Google Scholar] [CrossRef]
- Meher, N.; Iyer, P.K. Spontaneously Self-Assembled Naphthalimide Nanosheets: Aggregation-Induced Emission and Unveiling a-PET for Sensitive Detection of Organic Volatile Contaminants in Water. Angew. Chem. Int. Ed. 2018, 57, 8488–8492. [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]
- Yu, Y.; Xu, Z.; Zhao, Z.; Zhang, H.; Ma, D.; Lam, J.W.Y.; Qin, A.; Tang, B.Z. In Situ Generation of Red-Emissive AIEgens from Commercial Sources for Nondoped OLEDs. ACS Omega 2018, 3, 16347–16356. [Google Scholar] [CrossRef]
- Chen, S.; Li, X.; Song, L. A fluorescent photochromic diarylethene based on naphthalic anhydride with strong solvatochromism. RSC Adv. 2017, 7, 29854–29859. [Google Scholar] [CrossRef] [Green Version]
- Chipem, F.A.S.; Mishra, A.; Krishnamoorthy, G. The role of hydrogen bonding in excited state intramolecular charge transfer. Phys. Chem. Chem. Phys. 2012, 14, 8775–8790. [Google Scholar] [CrossRef]
- Mei, J.; Wang, J.; Sun, J.Z.; Zhao, H.; Yuan, W.; Deng, C.; Chen, S.; Sung, H.; Herman, H.Y.; Lu, P.; et al. Siloles symmetrically substituted on their 2,5-positions with electronaccepting and donating moieties: facile synthesis, aggregation-enhanced emission, solvatochromism, and device application. Chem. Sci. 2012, 3, 549–558. [Google Scholar] [CrossRef]
- Ding, D.; Li, K.; Liu, B.; Tang, B.Z. Bioprobes Based on AIE Fluorogens. Acc Chem. Res. 2013, 46, 2441–2453. [Google Scholar] [CrossRef]
- Zhang, X.; Wang, K.; Liu, M.; Zhang, X.; Tao, L.; Chena, Y.; Wei, Y. Polymeric AIE-based nanoprobes for biomedical applications: recent advances and perspectives. Nanoscale 2015, 7, 11486–11508. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Samples of the compounds AIE-1 and AIE-2 are available from the authors. |
© 2020 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 (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Tarai, A.; Huang, M.; Das, P.; Pan, W.; Zhang, J.; Gu, Z.; Yan, W.; Qu, J.; Yang, Z. ICT and AIE Characteristics Two Cyano-Functionalized Probes and Their Photophysical Properties, DFT Calculations, Cytotoxicity, and Cell Imaging Applications. Molecules 2020, 25, 585. https://doi.org/10.3390/molecules25030585
Tarai A, Huang M, Das P, Pan W, Zhang J, Gu Z, Yan W, Qu J, Yang Z. ICT and AIE Characteristics Two Cyano-Functionalized Probes and Their Photophysical Properties, DFT Calculations, Cytotoxicity, and Cell Imaging Applications. Molecules. 2020; 25(3):585. https://doi.org/10.3390/molecules25030585
Chicago/Turabian StyleTarai, Arup, Meina Huang, Pintu Das, Wenhui Pan, Jianguo Zhang, Zhenyu Gu, Wei Yan, Junle Qu, and Zhigang Yang. 2020. "ICT and AIE Characteristics Two Cyano-Functionalized Probes and Their Photophysical Properties, DFT Calculations, Cytotoxicity, and Cell Imaging Applications" Molecules 25, no. 3: 585. https://doi.org/10.3390/molecules25030585