Synthesis and Luminescence Behavior of a Novel Charge Transfer Compound Containing Carbazole Phenylhydrazone

doi:10.3724/SP.J.1095.2013.20571

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

Synthesis and Luminescence Behavior of a Novel Charge Transfer Compound Containing Carbazole Phenylhydrazone

LI Junfen¹, LI Jinzeng¹, ZHANG Caihong¹, HAN Yuying¹, QIN Xi¹, DONG Chuan^2*

(1.School of Chemistry and Chemical Engineering，Shanxi University，Taiyuan 030006，China;
2.Research Center of Environmental Science and Engineering，Shanxi University，Taiyuan 030006，China)

Received:2012-12-10 Revised:2013-01-21 Published:2013-10-10 Online:2013-10-10
Contact: dong

Abstract

Abstract: A novel compound, containing a strong electron donor and a strong electron acceptor，3-((2-(2,4-dinitrophenyl)hydrazono)methyl)-9-ethyl-9-H-carbazole, was synthesized. Its spectral property and photo-physical behavior were studied. Intermolecular charge transfer occurred from N-ethylcarbazole to NO2— with the increase of the solvent polarity. Double fluorescence emission was observed in strong polarity solvent. Change of dipole moment between the ground state and the excitation state was 4.53 D. Dimmer or polymer was formed at high concentration and the emission wavelength was red shifted.

Key words: Carbazole hydrazone compounds, Intramolecular charge transfer, Solvent polarity

CLC Number:

O656

LI Junfen1, LI Jinzeng1, ZHANG Caihong1, HAN Yuying1, QIN Xi1, DONG Chuan2*. Synthesis and Luminescence Behavior of a Novel Charge Transfer Compound Containing Carbazole Phenylhydrazone[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20571.

References

[1] Eléna I,Régis G,Guy B,et al. Photoinduced Intramolecular Charge-transfer Dynamics of a Red-emitting Dicyanovinyl-based Triarylamine Dye in Solution[J]. J Photochem Photobiol,A,2012,234(15):27-36.

[2] Manjunatha M G,Adhikari A V,Hegde P K,et al. A New Nonlinear Optically Active Donor-Acceptor-Type Conjugated Polymer:Synthesis and Electrochemical and Optical Characterization[J]. J Electron Mater,2010,39(12):2711-2719.

[3] Cao D X,Liu Z Q,Li G Z,et al. Synthesis and Blue-violet Two-photon Excited Fluorescence of a New Organoboron Compound[J]. J Mol Struct,2008,874:46-50.

[4] Bai G,Li J F,Li D X,et al. Synthesis and Spectrum Characteristic of Four New Organic Fluorescent Dyes of Pyrazoline Compounds[J]. Dyes Pigm,2007,75(1):93-98.

[5] Dong B,Zheng L Q,Xu J K,et al. Self-aggregation Behavior of Fluorescent Carbazole-tailed Imidazoliumonic Liquids in Aqueous Solutions[J]. J Phys Chem B,2010,114:340-348.

[6] Albrecht K,Yamamoto K. Dendritic Structure Having a Potential Gradient: New Synthesis and Properties of Carbazole Dendrimers[J]. J Am Chem Soc,2009,131(6):2244-2251.

[7] Khalil O S,Hofeldt R H,McGlynn S P. Electronic Spectroscopy of Highly-polar Aromatics:Molecular Interactions in the Ground and Excited States of N,N-dimethyl-p-cyanoaniline[J]. Chem Phys Lett,1972,17(4):479-481.

[8] Weisenborn P C M,Varma C A,De Haas M P,et al. Dipole Moments of Electronically Excited States of 4-N,N-Dimethylaminobenzonitrile and Related Compounds Deduced from Transient Dielectric Losses[J]. Chem Phys Lett,1986,129(6):562-568.

[9] Li J F,Bai G,Li D X,et al. Study on the Fluorescence Properties of a New Intramolecular Charge Transfer Compound 15-Diphenyl-3-(N-ethylcarbazole-3-yl)-2-pyrazoline[J]. Spectrochim Acta Part A,2007,68:404-408.

[10] Hicks J,Vandersall M,Babaogic Z,et al. Polarity-dependent Barriers and the Photoisomerization Dynamics of Molecules in Solution[J]. Chem Phys Lett,1987,135(4/5):413-420.

[11] Lakowicz J R. Principles of Fluorescence Spectroscopy[M]. 2nd Ed. New York:Kluwer Academic Plenum Publishers,1999.

[12] Dey J,Warner I M. Charge-transfer Effects on the Fluorescence Spectra of 9-Aminocamptothecin Steady-state and Time-resolved Fluorescence Studies[J]. J Photochem Photobiol A,1998,116(1):27-37.

Synthesis and Luminescence Behavior of a Novel Charge Transfer Compound Containing Carbazole Phenylhydrazone

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 7

Recommended Articles

Metrics

Comments

[1]	WU Yunxia1,2, HUANG Jing1,2, YIN Zhengzhi2, ZENG Yanbo2, ZHANG Zulei2, LI Lei2*. Properties of Rhodamine B′ Magnetic Molecularly Imprinted Polymers Prepared from the Suspension Polymerization Method [J]. Chinese Journal of Applied Chemistry, 2013, 30(12): 1481-1488.
[2]	XIONG Xiaoqin*, ZHAI Qiuge, XUE Lingfen, ZHENG Fei, XIE Xu. Synthesis of Styrylpyrimidine and Its Spectral Characteristic as a pH Probe [J]. Chinese Journal of Applied Chemistry, 2012, 29(11): 1262-1265.
[3]	ZENG Zhi1,2*, FU Lin1, YE Xuening1, ZHANG Tao3, MENG Shaojin1, MENG Chunyan1. Comparative of Volatile Oil Components from Fructus Amomi Rotundus, Fructus Galangae, Semen Alpiniae Katsumadai and Semen Myristicae [J]. Chinese Journal of Applied Chemistry, 2012, 29(11): 1316-1323.
[4]	ZHANG Daihui1,2*, LU Lijun1, ZHANG Xun1, MU Jun1, ZHOU Xiao1, HU Tingting1, HAN Dachuan1. Simultaneous Determination of Ten Kinds of Perfluorinated Compounds in Lubricant Samples by High-performance Liquid Chromatography-Tandem Mass Spectrometry [J]. Chinese Journal of Applied Chemistry, 2012, 29(10): 1163-1170.
[5]	ZENG Zhi1,2, YE Xuening1, PANG Shimin1, ZHANG Tao2,3, SHEN Miaoting1. Comparison of the Volatile Oil Components from Atractylodes chinensis* (DC.) Koidz. and Atractylodes lancea (Thunb.) DC. [J]. Chinese Journal of Applied Chemistry, 2012, 29(04): 470-476.
[6]	ZENG Zhi1,2*, XIE Runqian1, TAN Lixian1, ZHANG Tao3. GC-MS Analysis and Determination of Chemical Components of the Extracts from Ligusticum Chuanxiong Hort. by Steam Distillation and Supercritical CO₂ Extraction [J]. Chinese Journal of Applied Chemistry, 2011, 28(08): 956-962.
[7]	ZHANG Yuan, LI Yang, CHEN Bo, ZHU Bingyu, LIU Feng*. Effects of Bentonite Modified by Organic Additives on the Physical Stability of Hexaconazole Suspension [J]. Chinese Journal of Applied Chemistry, 2011, 28(05): 565-570.