D-A solid emitter with crowded and remarkably twisted conformations exhibiting multifunctionality and multicolor mechanochromism

Journal of Physical Chemistry C

Volumn 118, Issue 20, 2014, Pages 10998-11005

  Gong, Yongyang ^a   Zhang, Yiren ^a   Yuan, Wang Zhang ^a   Sun, Jing Zhi ^b   Zhang, Yongming ^a  

^a Shanghai Jiao Tong University   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

OPTOELECTRONIC DEVICES;

AGGREGATION-INDUCED EMISSIONS; EXTERNAL QUANTUM EFFICIENCY; INTRA-MOLECULAR CHARGE TRANSFER; MECHANICAL GRINDING; OPTO-ELECTRONIC MATERIALS; OPTOELECTRONIC APPLICATIONS; TWISTED CONFORMATION; TWO-PHOTON ABSORPTIONS;

TWO PHOTON PROCESSES;

EID: 84901378100     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp500556p     Document Type: Article

References (44)

1. Gu, C.; Dong, W.; Yao, L.; Lv, Y.; Zhang, Z.; Lu, D.; Ma, Y. Cross-Linked Multifunctional Conjugated Polymers Prepared by In Situ Electrochemical Deposition for a Highly-Efficient Blue-Emitting and Electron-Transport Layer Adv. Mater. 2012, 24, 2413-2417
2. Wilson, J. S.; Frampton, M. J.; Michels, J. J.; Sardone, L.; Marletta, G.; Friend, R. H.; Samorì, P.; Anderson, H. L.; Cacialli, F. Supramolecular Complexes of Conjugated Polyelectrolytes with Poly(ethylene oxide): Multifunctional Luminescent Semiconductors Exhibiting Electronic and Ionic Transport Adv. Mater. 2005, 17, 2659-2663 (Pubitemid 41677567)
3. Coronado, E.; Palomares, E. Hybrid Molecular Materials for Optoelectronic Devices J. Mater. Chem. 2005, 15, 3593-3597 (Pubitemid 41417052)
4. Sun, X.; Liu, Y.; Xu, X.; Yang, C.; Yu, G.; Chen, S.; Zhao, Z.; Qiu, W.; Li, Y.; Zhu, D. Novel Electroactive and Photoactive Molecular Materials Based on Conjugated Donor-Acceptor Structures for Optoelectronic Device Applications J. Phys. Chem. B 2005, 109, 10786-10792 (Pubitemid 40844512)
5. Zrazhevskiy, P.; Sena, M.; Gao, X. Designing Multifunctional Quantum Dots for Bioimaging, Detection, and Drug Delivery Chem. Soc. Rev. 2010, 39, 4326-4354
6. An, B.-K.; Gierschner, J.; Park, S. Y. π-Conjugated Cyanostilbene Derivatives: A Unique Self-Assembly Motif for Molecular Nanostructures with Enhanced Emission and Transport Acc. Chem. Res. 2011, 45, 544-554
7. Sasabe, H.; Kido, J. Multifunctional Materials in High-Performance OLEDs: Challenges for Solid-State Lighting Chem. Mater. 2010, 23, 621-630
8. Shirota, Y. Photo- and Electroactive Amorphous Molecular Materials-Molecular Design, Syntheses, Reactions, Properties, and Applications J. Mater. Chem. 2005, 15, 75-93 (Pubitemid 40147700)
9. Shen, X. Y.; Yuan, W. Z.; Liu, Y.; Zhao, Q.; Lu, P.; Ma, Y.; Williams, I. D.; Qin, A.; Sun, J. Z.; Tang, B. Z. Fumaronitrile-Based Fluorogen: Red to Near-Infrared Fluorescence, Aggregation-Induced Emission, Solvatochromism, and Twisted Intramolecular Charge Transfer J. Phys. Chem. C 2012, 116, 10541-10547
10. Shen, X. Y.; Wang, Y. J.; Zhao, E.; Yuan, W. Z.; Liu, Y.; Lu, P.; Qin, A.; Ma, Y.; Sun, J. Z.; Tang, B. Z. Effects of Substitution with Donor-Acceptor Groups on the Properties of Tetraphenylethene Trimer: Aggregation-Induced Emission, Solvatochromism, and Mechanochromism J. Phys. Chem. C 2013, 117, 7334-7347
11. Kim, F. S.; Guo, X.; Watson, M. D.; Jenekhe, S. A. High-mobility Ambipolar Transistors and High-gain Inverters from a Donor-Acceptor Copolymer Semiconductor Adv. Mater. 2010, 22, 478-482
12. Lin, T.-C.; He, G. S.; Zheng, Q.; Prasad, P. N. Degenerate Two-/Three-Photon Absorption and Optical Power-Limiting Properties in Femtosecond Regime of a Multi-Branched Chromophore J. Mater. Chem. 2006, 16, 2490-2498
13. Jiang, Y.; Wang, Y.; Hua, J.; Tang, J.; Li, B.; Qian, S.; Tian, H. Multibranched Triarylamine End-Capped Triazines with Aggregation-Induced Emission and Large Two-Photon Absorption Cross-Sections Chem. Commun. 2010, 46, 4689-4691
14. Wang, B.; Wang, Y.; Hua, J.; Jiang, Y.; Huang, J.; Qian, S.; Tian, H. Starburst Triarylamine Donor-Acceptor-Donor Quadrupolar Derivatives Based on Cyano-Substituted Diphenylaminestyrylbenzene: Tunable Aggregation-Induced Emission Colors and Large Two-Photon Absorption Cross Sections Chem.-Eur. J. 2011, 17, 2647-2655
15. Dou, C.; Han, L.; Zhao, S.; Zhang, H.; Wang, Y. Multi-Stimuli-Responsive Fluorescence Switching of a Donor-Acceptor π-Conjugated Compound J. Phys. Chem. Lett. 2011, 2, 666-670
16. Kulkarni, A. P.; Zhu, Y.; Babel, A.; Wu, P.-T.; Jenekhe, S. A. New Ambipolar Organic Semiconductors. 2. Effects of Electron Acceptor Strength on Intramolecular Charge Transfer Photophysics, Highly Efficient Electroluminescence, and Field-Effect Charge Transport of Phenoxazine-Based Donor-Acceptor Materials Chem. Mater. 2008, 20, 4212-4223
17. Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Highly Efficient Organic Light-Emitting Diodes from Delayed Fluorescence Nature 2012, 492, 234-238
18. Tanaka, H.; Shizu, K.; Miyazaki, H.; Adachi, C. Efficient Green Thermally Activated Delayed Fluorescence (TADF) from a Phenoxazine-Triphenyltriazine (PXZ-TRZ) Derivative Chem. Commun. 2012, 48, 11392-11394
19. Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and Structures Chem. Rev. 2003, 103, 3899-4032
20. Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D. Aggregation-Induced Emission of 1-Methyl-1,2,3,4,5-pentaphenylsilole Chem. Commun. 2001, 1740-1741 (Pubitemid 32906757)
21. Hu, R.; Lager, E.; Aguilar-Aguilar, A.; Liu, J.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Zhong, Y.; Wong, K. S.; Peña-Cabrera, E. Twisted Intramolecular Charge Transfer and Aggregation-Induced Emission of BODIPY Derivatives J. Phys. Chem. C 2009, 113, 15845-15853
22. Yuan, W. Z.; Lu, P.; Chen, S.; Lam, J. W. Y.; Wang, Z.; Liu, Y.; Kwok, H. S.; Ma, Y.; Tang, B. Z. Changing the Behavior of Chromophores from Aggregation-Caused Quenching to Aggregation-Induced Emission: Development of Highly Efficient Light Emitters in the Solid State Adv. Mater. 2010, 22, 2159-2163
23. Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Aggregation-Induced Emission Chem. Soc. Rev. 2011, 40, 5361-5388
24. Zhao, Z.; Lam, J. W. Y.; Tang, B. Z. Tetraphenylethene: a Versatile AIE Building Block for the Construction of Efficient Luminescent Materials for Organic Light-Emitting Diodes J. Mater. Chem. 2012, 22, 23726-23740
25. Yuan, W. Z.; Gong, Y.; Chen, S.; Shen, X. Y.; Lam, J. W. Y.; Lu, P.; Lu, Y.; Wang, Z.; Hu, R.; Xie, N. Efficient Solid Emitters with Aggregation-Induced Emission and Intramolecular Charge Transfer Characteristics: Molecular Design, Synthesis, Photophysical Behaviors, and OLED Application Chem. Mater. 2012, 24, 1518-1528
26. Li, W.; Liu, D.; Shen, F.; Ma, D.; Wang, Z.; Feng, T.; Xu, Y.; Yang, B.; Ma, Y. A Twisting Donor-Acceptor Molecule with an Intercrossed Excited State for Highly Efficient, Deep-Blue Electroluminescence Adv. Funct. Mater. 2012, 22, 2797-2803
27. Chi, Z.; Zhang, X.; Xu, B.; Zhou, X.; Ma, C.; Zhang, Y.; Liu, S.; Xu, J. Recent Advances in Organic Mechanofluorochromic Materials Chem. Soc. Rev. 2012, 41, 3878-3896
28. Weder, C. Mechanoresponsive Materials J. Mater. Chem. 2011, 21, 8235-8236
29. Kwon, M. S.; Gierschner, J.; Yoon, S.-J.; Park, S. Y. Unique Piezochromic Fluorescence Behavior of Dicyanodistyrylbenzene Based Donor-Acceptor-Donor Triad: Mechanically Controlled Photo-Induced Electron Transfer (eT) in Molecular Assemblies Adv. Mater. 2012, 24, 5487-5492
30. Kishimura, A.; Yamashita, T.; Yamaguchi, K.; Aida, T. Rewritable Phosphorescent Paper by the Control of Competing Kinetic and Thermodynamic Self-Assembling Events Nat. Mater. 2005, 4, 546-549 (Pubitemid 40952750)
31. Ciardelli, F.; Ruggeri, G.; Pucci, A. Dye-Containing Polymers: Methods for Preparation of Mechanochromic Materials Chem. Soc. Rev. 2013, 42, 857-870
32. Gong, Y.; Tan, Y.; Liu, J.; Lu, P.; Feng, C.; Yuan, W. Z.; Lu, Y.; Sun, J. Z.; He, G.; Zhang, Y. Twisted D-π-A Solid Emitters: Efficient Emission and High Contrast Mechanochromism Chem. Commun. 2013, 49, 4009-4011
33. Yuan, W. Z.; Tan, Y.; Gong, Y.; Lu, P.; Lam, J. W. Y.; Shen, X. Y.; Feng, C.; Sung, H. H. Y.; Lu, Y.; Williams, I. D. Synergy between Twisted Conformation and Effective Intermolecular Interactions: Strategy for Efficient Mechanochromic Luminogens with High Contrast Adv. Mater. 2013, 25, 2837-2843
34. Luo, X.; Li, J.; Li, C.; Heng, L.; Dong, Y. Q.; Liu, Z.; Bo, Z.; Tang, B. Z. Reversible Switching of the Emission of Diphenyldibenzofulvenes by Thermal and Mechanical Stimuli Adv. Mater. 2011, 23, 3261-3265
35. Xu, B.; Xie, M.; He, J.; Xu, B.; Chi, Z.; Tian, W.; Jiang, L.; Zhao, F.; Liu, S.; Zhang, Y. An Aggregation-Induced Emission Luminophore with Multi-Stimuli Single- and Two-Photon Fluorescence Switching and Large Two-Photon Absorption Cross Section Chem. Commun. 2013, 49, 273-275
36. Luo, X.; Zhao, W.; Shi, J.; Li, C.; Liu, Z.; Bo, Z.; Dong, Y. Q.; Tang, B. Z. Reversible Switching Emissions of Tetraphenylethene Derivatives among Multiple Colors with Solvent Vapor, Mechanical, and Thermal Stimuli J. Phys. Chem. C 2012, 116, 21967-21972
37. Sagara, Y.; Kato, T. Brightly Tricolored Mechanochromic Luminescence from a Single-Luminophore Liquid Crystal: Reversible Writing and Erasing of Images Angew. Chem. 2011, 123, 9294-9298
38. Dong, Y.; Xu, B.; Zhang, J.; Tan, X.; Wang, L.; Chen, J.; Lv, H.; Wen, S.; Li, B.; Ye, L. Piezochromic Luminescence Based on the Molecular Aggregation of 9,10-Bis((E)-2-(pyrid-2-yl)vinyl)anthracene Angew. Chem., Int. Ed. 2012, 51, 10782-10785
39. Ma, Z.; Teng, M.; Wang, Z.; Yang, S.; Jia, X. Mechanically Induced Multicolor Switching Based on a Single Organic Molecule Angew. Chem., Int. Ed. 2013, 52, 12268-12272
40. Wang, S.; Oldham, W. J.; Hudack, R. A.; Bazan, G. C. Synthesis, Morphology, and Optical Properties of Tetrahedral Oligo(phenylenevinylene) Materials J. Am. Chem. Soc. 2000, 122, 5695-5709 (Pubitemid 30432272)
41. Yamamoto, T.; Nishiyama, M.; Koie, Y. Palladium-Catalyzed Synthesis of Triarylamines from Aryl halides and Diarylamines Tetrahedron Lett. 1998, 39, 2367-2370 (Pubitemid 28167966)
42. Kim, S.; Zheng, Q.; He, G. S.; Bharali, D. J.; Pudavar, H. E.; Baev, A.; Prasad, P. N. Aggregation-Enhanced Fluorescence and Two-Photon Absorption in Nanoaggregates of a 9,10-Bis[4'-(4-aminostyryl)styryl]anthracene Derivative Adv. Funct. Mater. 2006, 16, 2317-2323 (Pubitemid 46028494)
43. Pawlicki, M.; Collins, H. A.; Denning, R. G.; Anderson, H. L. Two-Photon Absorption and the Design of Two-Photon Dyes Angew. Chem., Int. Ed. 2009, 48, 3244-3266
44. Sheik-Bahae, M.; Said, A. A.; Wei, T. H.; Hagan, D. J.; Van Stryland, E. W. Sensitive Measurement of Optical Nonlinearities Using a Single Beam IEEE J. Quantum Electron. 1990, 26, 760-769 (Pubitemid 20714175)