Synthesis and Spectroscopic Behavior of 4-(Anthracen-9-yl)-6-(hexadecyloxy)-1,3,5-triazin-2-amine

doi:10.7517/j.issn.1674-0475.2009.05.325

Abstract

Abstract: 4-(Anthracen-9-yl)-6-(hexadecyloxy)-1,3,5-triazin-2-amine(AHTA) was synthesized in three steps with 2,4,6-trichloro-1,3,5-triazine as starting material.The title compound was confirmed by IR,1H NMR,13C NMR,MS,and HRMS.The spectroscopic behavior shows that the anthracene ring and triazine ring in AHTA are not coplanar at ground state.AHTA shows ICT state emission at excited state.Different from the case in solution,AHTA shows H-aggregation in both self-assembly film and LB film based on the intermolecular H-bonding interaction.

Key words: 4-(anthracen-9-yl)-6-(hexadecyloxy)-1,3,5-triazin-2-amine, fluorescence, LB film, H-aggregation

CLC Number:

LI Zong-yao, LI Jian-hui, ZHAO Chun-mei, WANG Hua. Synthesis and Spectroscopic Behavior of 4-(Anthracen-9-yl)-6-(hexadecyloxy)-1,3,5-triazin-2-amine[J]. Imaging Science and Photochemistry, 2009, 27(5): 325-333.

References

[1] Grzegorz B.Recent applications of 2,4,6-trichloro-1,3,5-triazine andits derivatives in organic synthesis[J].Tetra-hedron,2006,62:9507-9522.
[2] Murase T,Fujita M.Highly blue luminescent triazine-amine conjugated oligomers[J].J.Org.Chem.,2005,70(23):9269-9279.
[3] Hou B Y,Wang D X,Wang MX,et al.Synthesis and structure of upper-ri m1,3-alternate tetraoxacalix[2] arene[2] triazine azacrowns and change of cavityinresponse tofluoride anion[J].J.Org.Chem.,2007,72(14):5218-5226.
[4] Elbe F,Keck J,Kramer HE A,et al.Photochemical and photophysical deactivation of 2,4,6-triaryl-1,3,5-triazines[J].J.Phys.Chem.A,2000,104(35):8296-8306.
[5] 李建征,王俊,迟绍明,傅文甫.新型水溶性萘啶基荧光材料的制备及性能研究[J].影像科学与光化学(感光科学与光化学),2008,26(1):25-31.Li J Z,Wang J,Chi S M,Fu WF.The synthesis and study of novel water-soluble PAMN derivatives as fluorescentprobe material[J].Imaging Science and Photochemistry(Photographic Science and Photochemistry),2008,26(1):25-31.
[6] Wang L Q,Peng XJ.Water soluble fluorescent 3H-indocyaninesfor biological analysis[J].Photographic Science andPhotochemistry(Imaging Science and Photochemistry),2004,22(3):238.
[7] Bel man I B.Handbook of Fluorescence Spectra of Aromatic Molecules[M].2^nd ed.Academic Press,1971.
[8] 王华,张宝文,曹怡,徐莉.不同方位取代的二氰基乙烯基蒽的光谱行为的研究[J].化学研究,1997,8(3):1-7.Wang H,Zhang B W,Cao Y,Xu L.Astudy of spectroscopic behavior of anthracene substituted by dicyanovinyl in dif-ferent positions[J].Chemical Researches,1997,8(3):1-7.
[9] Damme M V,Hofkens J,De Schryver F C,et al.Solvent dynamics andintramolecular charge transfer in 4-Cyano-4′-butyloxybiphenyl(4COB)[J].Tetrahedron,l989,45(15):4693-4706.
[10] Kemnitz K,Tamai N,Yamazaki T,et al.Fluorescence decays and spectral properties of rhodamine Bin submono-,mono-,and multilayer systems[J].J.Phys.Chem.,1986,90(21):5094-5101.
[11] Shinbo K,Kaneko F,Kobayashi S.Adsorption of cyanine dyes and optical properties of phosphatidic acid Langmuirmonolayers and Langmuir-Blodgett fil ms[J].Thin Solid Fil ms,1994,243(1-2):630-633.
[12] 王文军,徐建华,刘秀,等.LB膜中聚集体的类型及其荧光特性研究[J].发光学报,2000,21(1):48-53.Wang WJ,Xu J H,Liu X,et al.Types andfluorescence characteristics of aggregatesin Langmuir-blodgett multilay-ers[J].Chinese Journal of Luminescence,2000,21(1):48-53.

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