Excited-State Intramolecular Proton Transfer Dyes with Dual-State Emission Properties: Concept, Examples and Applications
Abstract
:1. Introduction
2. Scope of This Short Review/Perspective
3. Examples of ESIPT/DSE Emitters
3.1. 2-(2′-Hydroxyphenylbenzazole) (HBX) Fluorophores
3.2. Other Fluorophores
4. Photophysical Properties
Dye | λabs (Sol.) (nm) | λem (Sol.) (nm) | Φf (Sol.) | Solv. | λem (Solid) (nm) | Φf (Solid) | Matrix | Ref |
---|---|---|---|---|---|---|---|---|
1 | 363 | 472 | 0.15 | CH2Cl2 | 473 | 0.12 | KBr | [62] |
2a | 353 | 496 | 0.51 | toluene | 470 | 0.36 | KBr | [62] |
2b | 347 | 482 | 0.54 | toluene | 460 | 0.39 | KBr | [62] |
2c | 346 | 479 | 0.49 | toluene | 488 | 0.68 | KBr | [62] |
2d | 368 | 507 | 0.53 | toluene | 490 | 0.30 | KBr | [62] |
3 | 330 | 458 | 0.31 | THF | 460 | 0.16 | powder | [63] |
4 | 328 | 486 | 0.20 | THF | 484 | 0.16 | crystal | [64] |
5 | 366 | 414/477 | 0.19 | benzene | 470 | 0.13 | KBr | [65] |
6a | 349 | 397/514 | 0.10 | toluene | 530 | 0.51 | KBr | [67] |
6b | 349 | 489 | 0.19 | toluene | 504 | 0.63 | KBr | [67] |
6c | 347 | 550 | 0.32 | Toluene | 504 | 0.60 | KBr | [67] |
6d | 332 | 519 | 0.23 | toluene | 503 | 0.68 | KBr | [67] |
6e | 368 | 550 | 0.30 | toluene | 547 | 0.48 | KBr | [67] |
7a | 371 | 537 | 0.38 | toluene | 527 | 0.76 | KBr | [68] |
7b | 373 | 551 | 0.43 | toluene | 532 | 0.61 | KBr | [69] |
7c | 370 | 530 | 0.52 | toluene | 526 | 0.58 | KBr | [69] |
7d | 368 | 539 | 0.49 | toluene | 534 | 0.70 | KBr | [70] |
7e | 371 | 535 | 0.32 | toluene | 530 | 0.82 | KBr | [70] |
7f | 340 | 538 | 0.28 | toluene | 514 | 0.53 | KBr | [70] |
7g | 345 | 513 | 0.11 | toluene | 504 | 0.66 | KBr | [70] |
8a | 332 | 497 | 0.12 | CH2Cl2 | 496 | 0.38 | KBr | [71] |
8b | 335 | 518 | 0.40 | CH2Cl2 | 505 | 0.38 | KBr | [71] |
8c | 347 | 520 | 0.58 | CH2Cl2 | 541 | 0.22 | KBr | [71] |
9 | 372 | 543 | 0.50 | CH2Cl2 | 563 | 0.29 | KBr | [71] |
10 | 397 | 452/520 | 0.37 | CHCl3 | 520 | 0.34 | powder | [72] |
11a | 378 | 570 | 0.22 | toluene | 558 | 0.52 | KBr | [69] |
11b | 378 | 490/582 | 0.15 | toluene | 574 | 0.48 | KBr | [62] |
12 | 362 | 520 | 0.49 | CH2Cl2 | 528 | 0.57 | 5-CB | [73] |
13 | 400 | 605 | 0.08 | toluene | 605 | 0.23 | Crystal | [74] |
14 | 376 | 444 | 0.65 | toluene | 465/527 | 0.22 | Film | [75] |
15 | 424 | 521 | 0.87 | toluene | 573 | 0.19 | KBr | [76] |
16 | 350 | 534 | 0.12 | PBS | 534 | 0.51 | powder | [77] |
17 | 400 | 600 | 0.34 | CH2Cl2 | 695 | 0.34 | powder | [78] |
18a | 307 | 466 | 0.38 | CH2Cl2 | 466 | 0.57 | powder | [79] |
18b | 325 | 479 | 0.63 | CH2Cl2 | 477 | 0.74 | powder | [79] |
19a | 322 | 471 | 0.25 | CH2Cl2 | 491 | 0.87 | powder | [80] |
19b | 303 | 452 | 0.25 | CH2Cl2 | 463 | 0.68 | powder | [80] |
19c | 326 | 468 | 0.56 | CH2Cl2 | 494 | 0.74 | powder | [80] |
19d | 321 | 457 | 0.53 | CH2Cl2 | 473 | 0.15 | powder | [80] |
20 | 450 | 481 | 0.17 | CHCl3 | 481 | 0.38 | powder | [72] |
21 | 370 | 425 | 0.47 | toluene | 530 | 0.31 | PS | [81] |
22 | 368 | 433 | 0.60 | toluene | 530 | 0.55 | PS | [81] |
23a | 407 | 490 | 0.68 | toluene | 467 | 0.88 | PMMA | [82] |
23b | 388 | 506 | 0.29 | toluene | 473 | 0.44 | PMMA | [82] |
23c | 436 | 593 | 0.64 | CH2Cl2 | 528 | 0.83 | PMMA | [82] |
23d | 396 | 532 | 0.56 | CH2Cl2 | 482 | 0.45 | PMMA | [82] |
24a | 366 | 520 | 0.48 | benzene | 535 | 0.11 | powder | [83] |
24b | 366 | 523 | 0.74 | benzene | 540 | 0.39 | powder | [83] |
24c | 380 | 512 | 0.69 | benzene | 523 | 0.42 | powder | [83] |
24d | 369 | 505 | 0.85 | benzene | 515 | 0.53 | powder | [83] |
24e | 362 | 510 | 0.51 | benzene | 495 | 0.25 | powder | [83] |
25 | 366 | 542 | 0.52 | benzene | 535 | 0.13 | powder | [83] |
26 | 388 | 521 | 0.75 | CH2Cl2 | 530 | 0.51 | crystal | [84] |
27a | 508/544 | 558/593 | 0.11 | toluene | 675 | 0.08 | crystal | [85] |
27b | 532/560 | 579/616 | 0.27 | toluene | 656 | 0.73 | crystal | [85] |
27c | 537/568 | 586/622 | 0.58 | toluene | 670 | 0.51 | crystal | [85] |
27d | 536/568 | 582/621 | 0.43 | toluene | 682 | 0.41 | crystal | [85] |
28 | 343 | 500/535 | 0.43 | CH2Cl2 | 544 | 0.54 | powder | [86] |
5. First-Principle Modelling
6. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- De Moliner, F.; Kielland, N.; Lavilla, R.; Vendrell, M. Modern Synthetic Avenues for the Preparation of Functional Fluorophores. Angew. Chem. Int. Ed. 2017, 56, 3758. [Google Scholar] [CrossRef] [PubMed]
- Levi, L.; Muller, T.J.J. Multicomponent syntheses of functional chromophores. Chem. Soc. Rev. 2016, 45, 2825. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Fu, Y.; Finney, N.S. Small-molecule fluorescent probes and their design. RSC Adv. 2018, 8, 29051–29061. [Google Scholar] [CrossRef] [Green Version]
- Gao, Y.; Hu, Y.; Liu, Q.; Li, X.; Li, X.; Kim, C.; James, T.D.; Li, J.; Chen, X.; Guo, Y. Two-Dimensional Design Strategy to Construct Smart Fluorescent Probes for the Precise Tracking of Senescence. Angew. Chem. Int. Ed. 2021, 60, 10756–10765. [Google Scholar] [CrossRef] [PubMed]
- Yin, J.; Huang, L.; Wu, L.; Li, J.; James, T.D.; Lin, W. Small molecule based fluorescent chemosensors for imaging the microenvironment within specific cellular regions. Chem. Soc. Rev. 2021, 50, 12098. [Google Scholar] [CrossRef] [PubMed]
- Singh, H.; Tiwari, K.; Tiwari, R.; Pramanik, S.K.; Das, A. Small Molecules as Fluorescent Probes for Monitoring Intracellular Enzymatic Transformations. Chem. Rev. 2019, 119, 11718. [Google Scholar] [CrossRef]
- Gao, M.; Yu, F.; Lv, C.; Choo, J.; Chen, L. Fluorescent chemical probes for accurate tumor diagnosis and targeting therapy. Chem. Soc. Rev. 2017, 46, 2237. [Google Scholar] [CrossRef]
- Wolfbeis, O.S. Fluorescent chameleon labels for bioconjugation and imaging of proteins, nucleic acids, biogenic amines and surface amino groups. Methods Appl. Fluoresc. 2021, 9, 042001. [Google Scholar] [CrossRef]
- Park, S.-H.; Kwon, N.; Lee, J.-H.; Yoon, J.; Shin, I. Synthetic ratiometric fluorescent probes for detection of ions. Chem. Soc. Rev. 2020, 49, 143. [Google Scholar] [CrossRef]
- Gui, R.; **, H.; Bu, X.; Fu, Y.; Wang, Z.; Liu, Q. Recent advances in dual-emission ratiometric fluorescence probes for chemo/biosensing and bioimaging of biomarkers. Coord. Chem. Rev. 2019, 282, 82. [Google Scholar] [CrossRef]
- Gsänger, M.; Bialas, D.; Huang, L.; Stolte, M.; Würthner, F. Organic Semiconductors based on Dyes and Color Pigments. Adv. Mater. 2016, 28, 3615. [Google Scholar] [CrossRef] [PubMed]
- Gong, J.; Sumathy, K.; Qiao, Q.; Zhou, Z. Review on dye-sensitized solar cells (DSSCs): Advanced techniques and research trends. Renew. Sustain. Energy Rev. 2017, 68, 234. [Google Scholar] [CrossRef]
- Matsuki, K.; Pu, J.; Takenobu, T. Recent Progress on Light-Emitting Electrochemical Cells with Nonpolymeric Materials. Adv. Funct. Mater. 2020, 30, 1908641. [Google Scholar] [CrossRef]
- Bera, M.K.; Pal, P.; Malik, S. Solid-state emissive organic chromophores: Design, strategy and building blocks. J. Mater. Chem. C 2020, 8, 788. [Google Scholar] [CrossRef]
- Shimizu, M.; Hiyama, T. Organic Fluorophores Exhibiting Highly Efficient Photoluminescence in the Solid State. Chem. Asian J. 2010, 5, 1516. [Google Scholar] [CrossRef]
- Gierschner, J.; Shi, J.; Milian-Medina, B.; Roca-Sanjuan, D.; Varghese, S.; Park, S.Y. Luminescence in Crystalline Organic Materials: From Molecules to Molecular Solids. Adv. Opt. Mater. 2021, 9, 2002251. [Google Scholar] [CrossRef]
- Tang, S.; Yang, T.; Zhao, Z.; Zhu, T.; Zhang, Q.; Hou, W.; Yuan, W.Z. Nonconventional luminophores: Characteristics, advancements and perspectives. Chem. Soc. Rev. 2021, 50, 12616. [Google Scholar] [CrossRef]
- Förster, T. Excimers. Angew. Chem. Int. Ed. 1969, 8, 333. [Google Scholar] [CrossRef]
- Tasior, M.; Kim, D.; Singha, S.; Krzeszewski, M.; Ahn, K.H.; Gryko, D.T. π-Expanded coumarins: Synthesis, optical properties and applications. J. Mater. Chem. C 2015, 3, 1421. [Google Scholar] [CrossRef]
- Mishra, A.; Behera, R.K.; Behera, P.K.; Mishra, B.K.; Behera, G.B. Cyanines during the 1990s: A Review. Chem. Rev. 2000, 100, 1973. [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. [Google Scholar] [CrossRef] [PubMed]
- Luo, J.; ** dynamics simulations. RSC Adv. 2016, 6, 85574. [Google Scholar] [CrossRef]
- Li, Y.; Wang, L.; Guo, X.; Zhang, J. A CASSCF/CASPT2 insight into excited-state intramolecular proton transfer of four imidazole derivatives. J. Comput. Chem. 2015, 36, 2374. [Google Scholar] [CrossRef]
- Li, C.-X.; Guo, W.-W.; **e, B.-B.; Cui, G. Photodynamics of oxybenzone sunscreen: Nonadiabatic dynamics simulations. J. Chem. Phys. 2016, 145, 074308. [Google Scholar] [CrossRef]
- Cammi, R.; Mennucci, B. Linear response theory for the polarizable continuum model. J. Chem. Phys. 1999, 110, 9877. [Google Scholar] [CrossRef]
- Caricato, M.; Mennucci, B.; Tomasi, J.; Ingrosso, F.; Cammi, R.; Corni, S.; Scalmani, G. Formation and relaxation of excited states in solution: A new time dependent polarizable continuum model based on time dependent density functional theory. J. Chem. Phys. 2006, 124, 124520. [Google Scholar] [CrossRef]
- Guido, C.A.; Chrayteh, A.; Scalmani, G.; Mennucci, B.; Jacquemin, D. Simple Protocol for Capturing Both Linear-Response and State-Specific Effects in Excited-State Calculations with Continuum Solvation Models. J. Chem. Theory Comput. 2021, 17, 5155. [Google Scholar] [CrossRef] [PubMed]
- Verite, P.M.; Guido, C.A.; Jacquemin, D. First-principles investigation of the double ESIPT process in a thiophene-based dye. Phys. Chem. Chem. Phys. 2019, 21, 2307. [Google Scholar] [CrossRef] [PubMed]
- Loco, D.; Gelfand, N.; Jurinovich, S.; Protti, S.; Mezzetti, A.; Mennucci, B. Polarizable QM/Classical Approaches for the Modeling of Solvation Effects on UV-Vis and Fluorescence Spectra: An Integrated Strategy. J. Phys. Chem. A 2018, 122, 390. [Google Scholar] [CrossRef] [PubMed]
- Nottoli, M.; Bondanza, M.; Lipparini, F.; Mennucci, B. An enhanced sampling QM/AMOEBA approach: The case of the excited state intramolecular proton transfer in solvated 3-hydroxyflavone. J. Chem. Phys. 2021, 154, 184107. [Google Scholar] [CrossRef] [PubMed]
- Zhang, Q.; Li, Y.; Cao, Z.; Zhu, C. Aggregation-induced emission spectra of triphenylamine salicylaldehyde derivatives via excited-state intramolecular proton transfer revealed by molecular spectral and dynamics simulations. RSC Adv. 2021, 11, 37171. [Google Scholar] [CrossRef]
- Wang, H.; Gong, Q.; Wang, G.; Dang, J.; Liu, F. Deciphering the Mechanism of Aggregation-Induced Emission of a Quinazolinone Derivative Displaying Excited-State Intramolecular Proton-Transfer Properties: A QM, QM/MM, and MD Study. J. Chem. Theory Comput. 2019, 15, 5440. [Google Scholar] [CrossRef]
- Presti, D.; Labat, F.; Pedone, A.; Frisch, M.J.; Hratchian, H.P.; Ciofini, I.; Menziani, M.C.; Adamo, C. Modeling emission features of salicylidene aniline molecular crystals: A QM/QM’ approach. J. Comput. Chem. 2016, 37, 861. [Google Scholar] [CrossRef] [Green Version]
- Dommett, M.; Rivera, M.; Crespo-Otero, R. How Inter- and Intramolecular Processes Dictate Aggregation-Induced Emission in Crystals Undergoing Excited-State Proton Transfer. J. Phys. Chem. Lett. 2017, 8, 6148. [Google Scholar] [CrossRef]
- Mancini, D.T.; Sen, K.; Barbatti, M.; Thiel, W.; Ramalho, T.C. Excited-State Proton Transfer Can Tune the Color of Protein Fluorescent Markers. Chem. Phys. Chem. 2015, 16, 3444. [Google Scholar] [CrossRef] [Green Version]
- Zhao, J.; Dong, H.; Yang, H.; Zheng, Y. Aggregation Promotes Excited-State Intramolecular Proton Transfer for Benzothiazole-Substituted Tetraphenylethylene Compound. ACS Appl. Bio Mater. 2019, 2, 5182. [Google Scholar] [CrossRef]
- Presti, D.; Pedone, A.; Ciofini, I.; Labat, F.; Menziani, M.C.; Adamo, C. Optical properties of the dibenzothiazolylphenol molecular crystals through ONIOM calculations: The effect of the electrostatic embedding scheme. Theor. Chim. Acta 2016, 135, 1–11. [Google Scholar] [CrossRef] [Green Version]
- Presti, D.; Wilbraham, L.; Targa, C.; Labat, F.; Pedone, A.; Menziani, M.C.; Ciofini, I.; Adamo, C. Understanding Aggregation-Induced Emission in Molecular Crystals: Insights from Theory. J. Phys. Chem. C 2017, 121, 5847. [Google Scholar] [CrossRef]
- Rivera, M.; Dommett, M.; Crespo-Otero, R. ONIOM(QM:QM’) electrostatic embedding schemes for photochemistry in molecular crystals. J. Chem. Theory Comput. 2019, 15, 2504. [Google Scholar] [CrossRef] [PubMed]
- Rivera, M.; Dommett, M.; Sidat, A.; Rahim, W.; Crespo-Otero, R. fromage: A library for the study of molecular crystal excited states at the aggregate scale. J. Comput. Chem. 2020, 41, 1045. [Google Scholar] [CrossRef] [PubMed]
- Dommett, M.; Rivera, M.; Smith, M.T.H.; Crespo-Otero, R. Molecular and crystalline requirements for solid state fluorescence exploiting excited state intramolecular proton transfer. J. Mater. Chem. C 2020, 8, 2558. [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
Stoerkler, T.; Pariat, T.; Laurent, A.D.; Jacquemin, D.; Ulrich, G.; Massue, J. Excited-State Intramolecular Proton Transfer Dyes with Dual-State Emission Properties: Concept, Examples and Applications. Molecules 2022, 27, 2443. https://doi.org/10.3390/molecules27082443
Stoerkler T, Pariat T, Laurent AD, Jacquemin D, Ulrich G, Massue J. Excited-State Intramolecular Proton Transfer Dyes with Dual-State Emission Properties: Concept, Examples and Applications. Molecules. 2022; 27(8):2443. https://doi.org/10.3390/molecules27082443
Chicago/Turabian StyleStoerkler, Timothée, Thibault Pariat, Adèle D. Laurent, Denis Jacquemin, Gilles Ulrich, and Julien Massue. 2022. "Excited-State Intramolecular Proton Transfer Dyes with Dual-State Emission Properties: Concept, Examples and Applications" Molecules 27, no. 8: 2443. https://doi.org/10.3390/molecules27082443