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
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