A novel NIR violanthrone derivative with high
electron-deficiency: effect of fluorescence on dicyanomethylene substitution

doi:10.1007/s11458-010-0115-7

Front. Chem. China

2010, Vol. 5

Issue (2) : 200-207 https://doi.org/10.1007/s11458-010-0115-7

Research articles

A novel NIR violanthrone derivative with high electron-deficiency: effect of fluorescence on dicyanomethylene substitution

Bo LIU¹,Duo FAN²,Qiong ZHANG²,Yu CHEN²,Weihong ZHU²,

1.Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237, China；College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050016, China; 2.Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237, China;

Download: PDF(513 KB)
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract Near infrared (NIR) dyes attracted increasing interests in widely potential applications, such as fluorescent probe and living organism imaging, due to their low background signals from biomolecules, low light scattering and deep penetration, and low-cost excitation light sources. A novel NIR violanthrone derivative (VA-CN) with dicyanomethylene substitution was synthesized and fully characterized by ¹H NMR, ¹³C NMR, HRMS, and IR spectrometry. It is demonstrated that the original planar conformation of violanthrone ring (the nine fused benzene rings) becomes twisted and unsymmetrical upon the incorporation of two strong electron-withdrawing dicyanomethylene units. Photophysical, electrochemical performances as well as distinct solvatochromic effects were studied in detail. Considering the low reduction potential (−0.56 V vs NHE), VA-CN could be considered as a good electron acceptor due to the strong electron deficiency resulted from dicyanomethylene group. A distinct increase in fluorescence was observed with 30-fold enhancement upon the addition of n-butyl amine. The reversible fluorescence “off-on” shows that VA-CN might be served as a promising fluorescent sensor for electron-rich amines.

Keywords violanthrone derivative dicyanomethylene group synthesis NIR fluorescence

Issue Date: 05 June 2010

Cite this article:

Weihong ZHU,Bo LIU,Qiong ZHANG, et al. A novel NIR violanthrone derivative with high electron-deficiency: effect of fluorescence on dicyanomethylene substitution[J]. Front. Chem. China, 2010, 5(2): 200-207.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-010-0115-7
https://academic.hep.com.cn/fcc/EN/Y2010/V5/I2/200

	Umezawa, K.; Nakamura, Y.; Makino, H.; Citterio, D.; Suzuki, K., J. Am. Chem. Soc. 2008, 130, 1550―1551
	Weissleder, R., Nat. Biotechnol. 2001, 19, 316―317 doi: 10.1021/ja077756j
	Tang, B.; Cui, L. J.; Xu, K. H.; Tong, L. L.; Yang, G. W.; An, L. G., ChemBioChem2008, 9, 1159―1164 doi: 10.1038/86684
	Meguellati, K.; Spichty, M.; Ladame, S., Org. Lett. 2009, 11, 1123―1126 doi: 10.1002/cbic.200800001
	Lee, H.; Mason, J. C.; Achilefu, S., J. Org. Chem. 2008, 73, 723―725 doi: 10.1021/ol802913b
	Geiger, T.; Kuster, S.; Yum, J. H.; Moon, S. J.; Nazeeruddin, M. K.; Grätzel, M.; Nüesch, F., Adv. Funct. Mater. 2009, 19, 2720―2727 doi: 10.1021/jo701793h
	Dilek, G.; Akkaya, E. U., Tetrahedron Lett. 2000, 41, 3721―3724 doi: 10.1002/adfm.200900231
	Yagi, S.; Ohta, T.; Akagi, N.; Nakazumi, H., Dyes Pigments2008, 77, 525―536 doi: 10.1016/S0040-4039(00)00474-3
	Bae, J. S.; Gwon, S. Y.; Son, Y. A.; Kim, S. H., Dyes Pigments2009, 83, 324―327 doi: 10.1016/j.dyepig.2007.08.002
	Loudet, A.; Burgess, K., Chem. Rev. 2007, 107, 4891―4932 doi: 10.1016/j.dyepig.2009.05.010
	Wang, Y. W.; Yu, M. X.; Yu, Y. H.; Bai, Z. P.; Shen, Z.; Li, F. Y.; You, X. Z., Tetrahedron Lett. 2009, 50, 6169―6172 doi: 10.1021/cr078381n
	Tian, M.; Peng, X.; Feng, F.; Meng, S.; Fan, J.; Sun, S., Dyes Pigments2009, 81, 58―62 doi: 10.1016/j.tetlet.2009.08.078
	Hansongnern, K.; Chooto, P.; Amornpitoksuk, P., Int. J.Photoenergy1999, 1, 143―145 doi: 10.1016/j.dyepig.2008.09.004
	Inokuchi, H., Org. Electron. 2006, 7, 62―76 doi: 10.1155/S1110662X99000240
	Cabanillas-Gonzalez, J.; Yeates, S.; Bradley, D. D. C., Synth.Met. 2003, 139, 637―641 doi: 10.1016/j.orgel.2005.12.007
	Seybold, G.; Wagenblast, G., Dyes Pigments1989, 11, 303―317 doi: 10.1016/S0379-6779(03)00326-6
	Rauhut, M. M.; Roberts, B. G.; Maulding, D. R.; Bergmark, W.; Coleman, R., J. Org. Chem. 1975, 40, 330―335 doi: 10.1016/0143-7208(89)85048-X
	Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; et al, Gaussian 03, revisionC.01, Gaussian, Inc.: Pittsburgh, PA, 2004 doi: 10.1021/jo00891a014
	Becke, A. D., J. Chem. Phys. 1993, 98, 5648―5652
	Ditchfield, R.; Herhe, W. J.; Pople, J. A., J. Chem. Phys. 1971, 54, 724―728 doi: 10.1063/1.464913
	Isborn, C. M.; Leclercq, A.; Vila, F. D.; Dalton, L. R.; Brédas, J. L.; Eichinger, B. E.; Robinson, B. H., J. Phys. Chem. A2007, 111, 1319―1327 doi: 10.1063/1.1674902
	Liu, B.; Zhu, W. H.; Zhang, Q.; Wu, W. J.; Xu, M.; Ning, Z. J.; Xie, Y. S.; Tian, H., Chem. Commun. 2009, 1766―1768 doi: 10.1021/jp064096g
	Mishra, A.; Fischer, M. K. R.; Bäuerle, P., Angew. Chem. Int. Ed. 2009, 48, 2474―2499 doi: 10.1039/b820964b
	Suzuki, T.; Ichioka, K.; Higuchi, H.; Kawai, H.; Fujiwara, K.; Ohkita, M.; Tsuji, T.; Takahashi, Y., J. Org. Chem. 2005, 70, 5592―5598 doi: 10.1021/jo0505324
	Fabian, J.; Nakazumi, H.; Matsuoka, M., Chem. Rev. 1992, 92, 1197―1226 doi: 10.1021/cr00014a003
	Valeur, R., Molecular Fluorescence: Principles and Applications; Wiley-VCH: Verlag GmbH, 2001, p200―225
	Jacob, J.; Sax, S.; Piok, T.; List, E. J. W.; Grimsdale, A. C.; Müllen, K., J. Am. Chem. Soc. 2004, 126, 6987―6995 doi: 10.1021/ja0398823

[1]	Qiuyang SUN, Zhipan LIU. Mechanism and kinetics for methanol synthesis from CO₂/H₂ over Cu and Cu/oxide surfaces: Recent investigations by first-principles-based simulation[J]. Front Chem Chin, 2011, 6(3): 164-172.
[2]	Xiaojing LU, Yin PENG, . The first rare-earth fluoride one-dimensional nanostructures: template synthesis of LnF 3 (Ln=Eu, La) nanotubes[J]. Front. Chem. China, 2010, 5(1): 76-79.
[3]	Yanli SUN, Shiming WANG, Qiongsheng WANG. Flowerlike MoS₂ nanoparticles: solvothermal synthesis and characterization[J]. Front Chem Chin, 2009, 4(2): 173-176.
[4]	Fanzuo KONG. Synthesis of plant arabinogalactans[J]. Front Chem Chin, 2009, 4(1): 10-31.
[5]	Bozhou WANG, Weipeng LAI, Qian LIU, Peng LIAN, Yongqiang XUE. Synthesis, characterization and quantum chemistry study of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine[J]. Front Chem Chin, 2009, 4(1): 69-74.
[6]	Junzhen ZHANG, Bingqin YANG, Yating YANG, Binglin ZHANG. Synthesis, characterization and crystal structure of 1-ferrocenesulfonyl-2-long carbon chain alkyl benzimidazole[J]. Front Chem Chin, 2009, 4(1): 52-57.
[7]	PENG Yin, BAO Ling. Controlled-synthesis of ZnO nanorings[J]. Front. Chem. China, 2008, 3(4): 458-463.
[8]	WANG Cunwen, CHEN Wen, WANG Weiguo, WU Yuanxin, ZHANG Junfeng, YU Chuanbo. Calculation of partial molar volume of components in supercritical ammonia synthesis system [J]. Front. Chem. China, 2008, 3(4): 489-494.
[9]	LIU Xinhua, ZHU Jing, PAN Chunxiu, LI Bo, SONG Bao‘an. Synthesis and fungicidal activity of novel 3,5-diarylpyrazole derivatives[J]. Front. Chem. China, 2008, 3(4): 418-421.
[10]	HE Xiaoli, LU Lude, WANG Xin, YANG Xujie, HE Xiaoli, GUO Xuan. Synthesis and catalytic properties of tetraorganodistannoxanes containing silicon[J]. Front. Chem. China, 2008, 3(4): 413-417.
[11]	HE Gu, GUO Li, WANG Qianqian, MA Lifang, HE Zechao. Studies on synthesis and molecular dynamics simulation of dendrimers containing amino acids and peptides[J]. Front. Chem. China, 2007, 2(4): 378-382.
[12]	WU Yikang, WU Yu-Lin. A new era for organic synthesis—highlights of the recent progress[J]. Front. Chem. China, 2007, 2(3): 227-264.
[13]	CHEN Weimin, FENG Jin, TU Hongyi. Synthesis and antitumor activities of novel 2-substituted pyrimidinone-5-carboxylic acid benzylamides[J]. Front. Chem. China, 2007, 2(2): 127-130.
[14]	ZHANG Hua, LIU Jihong, XU Qiang. Synthesis and characterization of novel derivatives of triazinone[J]. Front. Chem. China, 2007, 2(2): 164-168.
[15]	LI Shuxin, ZHAO Yanjin, GUO Jinhua, WANG Zhiqing, JIANG Falong. An efficient method for the synthesis of 9-β-D-2′-deoxyribofuranosyl-6-methylpurine[J]. Front. Chem. China, 2007, 2(2): 218-221.

Viewed

Full text

Abstract

Cited

Shared

Discussed