Citation: ZHANG Li-Ping, CHAI Wan-Dong, JIN Rui-Fa. Rational Design of Star-shaped Molecules with Benzene Core and Naphthalimide Derivatives End Groups as Organic Light-emitting Materials[J]. Chinese Journal of Structural Chemistry, ;2016, 35(12): 1811-1818. doi: 10.14102/j.cnki.0254-5861.2011-1319 shu

Rational Design of Star-shaped Molecules with Benzene Core and Naphthalimide Derivatives End Groups as Organic Light-emitting Materials

a.
College of Physical and Electronic and Information Engineering, Chifeng University, Chifeng 024000, China
b.
Inner Mongolia Key Laboratory of Photoelectric Functional Materials, College of Chemistry and Chemical Engineering, Chifeng University, Chifeng 024000, China

Corresponding author: JIN Rui-Fa, Ruifajin@163.com
Received Date: 13 June 2016

Fund Project: Natural Science Foundation of Inner Mongolia Autonomous Region 2015MS0201Research Program of Sciences at Universities of Inner Mongolia Autonomous Region NJZZ235National Natural Science Foundation of China 21563002

Figures(2)

A series of star-shaped molecules with benzene core and naphthalimides derivatives end groups have been designed to explore their optical, electronic, and charge transport properties as charge transport and/or luminescent materials for organic light-emitting diodes (OLEDs). The frontier molecular orbitals (FMOs) analysis has turned out that the vertical electronic transitions of absorption and emission are characterized as intramolecular charge transfer (ICT). The calculated results show that the optical and electronic properties of star-shaped molecules are affected by the substituent groups in N-position of 1,8-naphthalimide ring. Our results suggest that star-shaped molecules with n-butyl (1), benzene (2), thiophene (3), thiophene S',S'-dioxide (4), benzo[c][1,2,5]thiadiazole (5), and 2,7a-dihydrobenzo[d]thiazole (6) fragments are expected to be promising candidates for luminescent and electron transport materials for OLEDs. This study should be helpful in further theoretical investigations on such kind of systems and also to the experimental study for charge transport and/or luminescent materials for OLEDs.
- 1,8-naphthalimide derivatives,
- optical and electronic properties,
- charge transport property,
- luminescent materials,
- organic light-emitting diodes (OLEDs)
1. [1]
  Müllen K, Scherf U. Organic Light-emitting Devices, Synthesis, Properties, and Applications[J]. Wiley-VCH, Weinheim, 2006.
2. [2]
  Minaev B, Baryshnikov G, Agren H. Principles of phosphorescent organic light emitting devices[J]. Phys. Chem. Chem. Phys, 2014,16:1719-1758. doi: 10.1039/C3CP53806K
3. [3]
  Sasabe H, Kido J. Development of high performance OLEDs for general lighting[J]. J. Mater. Chem. C, 2013,1:1699-1707. doi: 10.1039/c2tc00584k
4. [4]
  Che W. L, Liang W. D, Wang J, Lin G. X, Li G. F, Han C, Cui X. J, Zhu D. X. Synthesis, crystal structure and photoluminescence of triphenylamin derivative[J]. J. Mol. Sci, 2013,29:259-264.
5. [5]
  Han L. Z, Wang C. T, Ren A. M, Liu Y. L, Liu P. J. Structural and optical properties of triphenylamin-substitutef anthracene derivatives[J]. J. Mol. Sci, 2013,29:146-151.
6. [6]
  Jin R, ·Irfan A. Theoretical study on photophysical properties of multifunctional star-shaped molecules with 1,8-naphthalimide core for organic light-emitting diode and organic solar cell application[J]. Theor. Chem. Acc, 2015,13489. doi: 10.1007/s00214-015-1693-8
7. [7]
  Ramachandram B, Saroja G, Sankaran N. B, Samanta A. Unusually high fluorescence enhancement of some 1,8-naphthalimide derivatives induced by transition metal salts[J]. J. Phys. Chem. B, 2000,104:11824-11832. doi: 10.1021/jp000333i
8. [8]
  Ivanov I. P, Dimitrova M. B, Tasheva D. N, Cheshmedzhieva D. V, Lozanov V. S, Ilieva S. V. Synthesis, structural analysis and application of a series of solid-state fluorochromes-aryl hydrazones of 4-hydrazino-N-hexyl-1,8-naphthalimide[J]. Tetrahedron, 2013,69:712-721. doi: 10.1016/j.tet.2012.10.093
9. [9]
  Li Y, Xu Y, Qian X, Qu B. Naphthalimide-thiazoles as novel photonucleases: molecular design, synthesis, and evaluation[J]. Tetra. Lett, 2004,45:1247-1251. doi: 10.1016/j.tetlet.2003.11.145
10. [10]
  Grabchev I, Chovelon J. M, Qian X. A copolymer of 4-N,N-dimethylaminoethylene-N-allyl-1,8-naphthalimide with methylmethacrylate as a selective fluorescent chemosensor in homogeneous systems for metal cations[J]. J. Photochem. Photobiol. A, 2003,158:37-43. doi: 10.1016/S1010-6030(03)00100-X
11. [11]
  Morgado J, Gruner J, Walcott S. P, Yong T. M, Cervini R, Moratti S. C, Holmes A. B, Friend R. H, 4-AcNI—a new polymer for light-emitting diodes. Synth[J]. Met, 1998,95:113-117.
12. [12]
  Islam A, Cheng C. C, Chi S. H, Lee S. J, Hela G. P, Chen I. C, Cheng C. H. Aminonaphthalic anhydrides as red-emitting materials: electroluminescence, crystal structure, and photophysical properties[J]. J. Phys. Chem. B, 2005,109:5509-5517.
13. [13]
  Yang J. X, Wang X. L, Wang X. M, Xu L. H. The synthesis and spectral properties of novel 4-phenylacetylene-1,8-naphthalimide derivatives[J]. Dyes Pigm, 2005,66:83-87. doi: 10.1016/j.dyepig.2004.07.015
14. [14]
  Magalhaes J. L, Pereira R. V, Triboni E. R, Berci Filho P, Gehlen M. H, Nart F. C. Solvent effect on the photophysical properties of 4-phenoxy-N-methyl-1,8-naphthalimide[J]. J. Photochem. Photobiol. A, 2006,183:165-170. doi: 10.1016/j.jphotochem.2006.03.012
15. [15]
  Liu Y, Niu F, Lian J, Zeng P, Niu H. Synthesis and properties of starburst amorphous molecules: 1,3,5-tris(1,8-naphthalimide-4-yl)benzenes[J]. Synth. Met, 2010,160:2055-2060. doi: 10.1016/j.synthmet.2010.07.020
16. [16]
  Frisch , M. J, Trucks , G. W, Schlegel , H. B, Scuseria , G. E, Robb M. A, Cheeseman J. R, Scalmani G, Barone V, Mennucci B, Petersson G. A, Nakatsuji H, Caricato M, Li X, Hratchian H. P, Izmaylov A. F, Bloino J, Zheng G, Sonnenberg J. L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J. A, Peralta Jr. J. E, Ogliaro F, Bearpark M, Heyd J. J, Brothers E, Kudin K. N, Staroverov V. N, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J. C, Iyengar S. S, Tomasi J, Cossi M, Rega N, Millam J. M, Klene M, Knox J. E, Cross J. B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R. E, Yazyev O, Austin A. J, Cammi R, Pomelli C, Ochterski J. W, Martin R. L, Morokuma K, Zakrzewski V. G, Voth G. A, Salvador P, Dannenberg J. J, Dapprich S, Daniels A. D, Farkas O, Foresman J. B, Ortiz J. V, Cioslowski J, Fox D. J. Gaussian, Inc., Wallingford CT, 2009, Gaussian 09, Revision A[J]. , .
17. [17]
  Mancini G, Zazza C, Aschib M, Sannaa N. Conformational analysis and UV/Vis spectroscopic properties of a rotaxane-based molecular machine in acetonitrile dilute solution: when simulations meet experiments[J]. Phys. Chem. Chem. Phys, 2011,13:2342-2349. doi: 10.1039/C0CP01773F
18. [18]
  Li H, Li N, Sun R, Gu H, Ge J, Lu J, Xu Q, Xia X, Wang L. Dynamic random access memory devices based on functionalized copolymers with pendant hydrazine naphthalimide group[J]. J. Phys. Chem. C, 2011,115:8288-8294.
19. [19]
  Li Z, Yang Q, Chang R, Ma G, Chen M, Zhang W. N-Heteroaryl-1,8-naphthalimide fluorescent sensor for water: molecular design, synthesis and proper[J]. Dyes. Pigm, 2011,88:307-314. doi: 10.1016/j.dyepig.2010.07.009
20. [20]
  Gudeika D, Michaleviciute A, Grazulevicius J. V, Lygaitis R, Grigalevicius S, Jankauskas V, Miasojedovas A, Jursenas S, Sini G. Structure properties relationship of donor-acceptor derivatives of triphenylamine and 1,8-naphthalimide[J]. J. Phys. Chem. C, 2012,116:14811-14819. doi: 10.1021/jp303172b
21. [21]
  Pearson R. G. Absolute electronegativity and absolute hardness of Lewis acids and bases[J]. J. Am. Chem. Soc, 1985,107:6801-6806. doi: 10.1021/ja00310a009
22. [22]
  Start M. S. Epoxidation of alkenes by peroxyl radicals in the gas phase: structure-activity relationships[J]. J. Phys. Chem. A, 1997,101:8296-8301. doi: 10.1021/jp972054+
23. [23]
  Forés M, Duran M, Solà M, Adamowicz L. Excited-state intramolecular proton transfer and rotamerism of 2-(2′-hydroxyvinyl)benzimidazole and 2-(2′-hydroxyphenyl)imidazole[J]. J. Phys. Chem. A, 1999,103:4413-4420. doi: 10.1021/jp9844765
24. [24]
  Schleyer P, Von R, Allinger N. L, Clark T, Gasteiger J, Kollman P. A, III Schaefer H. F, Schreiners P. R. The Encyclopedia of Computational Chemistry[J]. Wiley, UK, Chichester, 1998.
25. [25]
  Marcus R. A. Electron transfer reactions in chemistry. theory and experiment[J]. Rev. Mod. Phys, 1993,65:599-610. doi: 10.1103/RevModPhys.65.599
26. [26]
  Marcus R. A. Chemical and electrochemical electron-transfer theory[J]. Annu. Rev. Phys. Chem, 1964,15:155-196. doi: 10.1146/annurev.pc.15.100164.001103
27. [27]
  Lemaur V, Steel M, Beljonne D, Brédas J. L, Cornil J. Photoinduced charge generation and recombination dynamics in model donor/acceptor pairs for organic solar cell applications: a full quantum-chemical treatment[J]. J. Am. Chem. Soc, 2005,127:6077-6076. doi: 10.1021/ja042390l
28. [28]
  Hutchison G. R, Ratner M. A, Marks T. J. Hopping transport in conductive heterocyclic oligomers: reorganization energies and substituent effects[J]. J. Am. Chem. Soc, 2005,127:2339-2350. doi: 10.1021/ja0461421
29. [29]
  Martinelli N. G, Idé J, Sánchez-Carrera R. S, Coropceanu V, Brédas J. L, Ducasse L, Castet F, Cornil J, Beljonne D. Influence of structural dynamics on polarization energies in anthracene single crystals[J]. J. Phys. Chem. C, 2010,114:20678-20685. doi: 10.1021/jp105843t
30. [30]
  McMahon D. P, Trois A. Evaluation of the external reorganization energy of polyacenes[J]. J. Phys. Chem. Lett, 2010,1:941-946. doi: 10.1021/jz1001049
31. [31]
  K?se M. E, Long H, Kim K, Graf P, Ginley D. Charge transport simulations in conjugated dendrimers[J]. J. Phys. Chem. A, 2010,114:4388-4393.
32. [32]
  Sakanoue K, Motoda M, Sugimoto M, Sakaki S. A molecular orbital study on the hole transport property of organic amine compounds[J]. J. Phys. Chem. A, 1999,103:5551-5556. doi: 10.1021/jp990206q
33. [33]
  K?se M. E, Mitchell W. J, Kopidakis N, Chang C. H, Shaheen S. E, Kim K, Rumbles G. Theoretical studies on conjugated phenyl-cored thiophene dendrimers for photovoltaic applications[J]. J. Am. Chem. Soc, 2007,129:14257-14270. doi: 10.1021/ja073455y
34. [34]
  Lin B. C, Cheng C. P, You Z. Q, Hsu C. P. Charge transport properties of tris(8-hydroxyquinolinato)aluminum(III): why it is an electron transporter[J]. J. Am. Chem. Soc, 2005,127:66-67. doi: 10.1021/ja045087t
35. [35]
  Gruhn N. E, da Silva Filho D. A, Bill T. G, Malagoli M, Coropceanu V, Kahn A, Brédas J. L. The vibrational reorganization energy in pentacene: molecular influences on charge transport[J]. J. Am. Chem. Soc, 2002,124:7918-7919. doi: 10.1021/ja0175892
1. [1]
  TANG Shan-Shan , LIU Jun-Bo , CHEN Guang , JIN Rui-Fa . Theoretical Study on Electronic and Charge Transfer Properties of Oligo[8]thiophene and Its Circular, Hooped, and Helical Derivatives. Chinese Journal of Structural Chemistry, 2014, 33(1): 104-114.
2. [2]
  WANG Yan , GAO Hui , YANG Ping , NIE Guang-Hua , SONG Xin-Jian . Theoretical Study on the Electronic Structures and Spectral Properties of 1,8-Naphthalimide Derivatives. Chinese Journal of Structural Chemistry, 2014, 33(6): 813-820.
3. [3]
  Zeng Yan , Duan Ruihong , Guo Yuan , Han Guangchao , Li Qingxu , Yi Yuanping . Electronic, optical, and charge transport properties of A-π-A electron acceptors for organic solar cells: Impact of anti-aromatic π structures. Chinese Chemical Letters, 2019, 30(1): 211-216. doi: 10.1016/j.cclet.2018.05.029
4. [4]
  Bo Hu , Chan Yao , Qing Wei Wang , Xu Ri Huang . The effect of diphenylamine on the electronic, optical, and charge transport properties of BTD-based derivative:Insights from theory. Chinese Chemical Letters, 2011, 22(11): 1383-1386. doi: 10.1016/j.cclet.2011.04.017
5. [5]
  Ting Zhang , Dong-Qing Xu , Jun-Ming Chen , Ping Zhang , Xu-Chun Wanga . Synthesis and characterization of carbazole-based dendrimers as bipolar host materials for green phosphorescent organic light emitting diodes. Chinese Chemical Letters, 2016, 27(03): 441-446. doi: 10.1016/j.cclet.2015.12.028
6. [6]
  Zhang Liang , Li Meng , Gao Qingyu , Chen Chuanfeng . Synthesis and Properties of New Organic Luminescent Materials Based on Halogen-Substituted Phthalimides. Chinese Journal of Organic Chemistry, 2020, 40(2): 516-520. doi: 10.6023/cjoc201909012
7. [7]
  ZHAO Pu-Su , JING Long , LI Yu-Feng , ZHU Yuan , WANG Jing , JIAN Fang-Fang . Comparative Studies on Two 1,8-Naphthalimide Derivatives with Experimental and Theoretical Methods. Chinese Journal of Structural Chemistry, 2014, 33(5): 676-686.
8. [8]
  Yan Zi'ang , Zou Lei , Ma Xiang . Recent Advances in Pure Organic Luminescent Supramolecular Materials. Chinese Journal of Organic Chemistry, 2020, 40(7): 1814-1822. doi: 10.6023/cjoc202004003
9. [9]
  Ablikim Obold , Ming Zhang , Feng Li . Evolution of emission manners of organic light-emitting diodes: From emission of singlet exciton to emission of doublet exciton. Chinese Chemical Letters, 2016, 27(8): 1345-1349. doi: 10.1016/j.cclet.2016.06.030
10. [10]
  Shi-Yang Shao , Jun-Qiao Ding , Li-Xiang Wang . New applications of poly(arylene ether)s in organic light-emitting diodes. Chinese Chemical Letters, 2016, 27(8): 1201-1208. doi: 10.1016/j.cclet.2016.07.006
11. [11]
  Yang Bing , Zhao Jianfeng , Wang Zepeng , Yang Zhenlin , Lin Zongqiong , Zhang Yanni , Li Jiewei , Xie Linghai , An Zhongfu , Zhang Hongmei , Weng Jiena , Huang Wei . Green-synthesized, low-cost tetracyanodiazafluorene (TCAF) as electron injection material for organic light-emitting diodes. Chinese Chemical Letters, 2019, 30(11): 1969-1973. doi: 10.1016/j.cclet.2019.08.054
12. [12]
  Yan Ma , Qian-Yun Tang , Ji Zhu , Li-Hong Wang , Cheng Yao . Fluorescent and thermal properties of siloxane-polyurethanes based on 1, 8-naphthalimide. Chinese Chemical Letters, 2014, 25(05): 680-686. doi: 10.1016/j.cclet.2014.01.048
13. [13]
  Hao Chen , Xing Xu , He Gang Yan , Xian Rong Cai , Ying Li , Qing Jiang , Ming Gui Xie . Novel fluorene-carzazole-based conjugated copolymers containing pyrazoline and benzothiazole segments for blue light-emitting materials. Chinese Chemical Letters, 2007, 18(12): 1496-1500. doi: 10.1016/j.cclet.2007.10.005
14. [14]
  Fu Zhiyuan , Wang Kai , Zou Bo . Recent advances in organic pressure-responsive luminescent materials. Chinese Chemical Letters, 2019, 30(11): 1883-1894. doi: 10.1016/j.cclet.2019.08.041
15. [15]
  QIN Yan-Yan , XU Wen-Juan , HU Chang-Yong , LIU Shu-Juan , ZHAO Qiang . Four-Coordinated Organoboron Compounds with π-Conjugated N, C-Chelate Ligand and Their Optoelectronic Applications. Chinese Journal of Inorganic Chemistry, 2017, 33(10): 1705-1721. doi: 10.11862/CJIC.2017.223
16. [16]
  Zhong Hui Li , Mo Jun Xiong , Man Shing Wong . Synthesis and blue light-emitting properties of 4, 4'-bis(diphenylamino)-quinque(p-phenyl)s. Chinese Chemical Letters, 2007, 18(7): 823-826. doi: 10.1016/j.cclet.2007.05.016
17. [17]
  Li Ma , Shan Wang , Xiao Feng , Bo Wang . Recent advances of covalent organic frameworks in electronic and optical applications. Chinese Chemical Letters, 2016, 27(8): 1383-1394. doi: 10.1016/j.cclet.2016.06.046
18. [18]
  Cheng Lu , Cao Yu , Ge Rui , Wei Ying-Qiang , Wang Na-Na , Wang Jian-Pu , Huang Wei . Sky-blue perovskite light-emitting diodes based on quasi-two-dimensional layered perovskites. Chinese Chemical Letters, 2017, 28(1): 29-31. doi: 10.1016/j.cclet.2016.07.001
19. [19]
  TAN Ying-Xiong , LIU Jian-Bo , LI Quan , ZHAO Ke-Qing . Charge Transfer Properties of Organic Semiconductor Molecules of Perylene Derivatives. Chinese Journal of Structural Chemistry, 2015, 34(3): 335-343. doi: 10.14102/j.cnki.0254-5861.2011-0312
20. [20]
  ZHAO Cai-Bin , GE Hong-Guang , JIN Ling-Xi , ZHANG Qiang , YIN Shi-Wei . Theoretical Investigation on the Charge Transport Properties of 2,5-Di(cyanovinyl)-thiophene/furan with the Kinetic Monte Carlo Method. Chinese Journal of Structural Chemistry, 2016, 35(5): 687-697. doi: 10.14102/j.cnki.0254-5861.2011-0803
Rational Design.docx

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(3951)
HTML views(260)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142