苯並三唑類(Benzotriazole)紫外光吸收劑之合成與定性

邱丞偉

doi:10.6844/NCKU.2013.00823

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苯並三唑類(Benzotriazole)紫外光吸收劑之合成與定性

Synthesis and Characterization of Benzotriazole Basis UV Absorbents

邱丞偉 , Masters　　Advisor：黃福永　　

繁體中文 DOI： 10.6844/NCKU.2013.00823

2-(2’-羥基-5’-叔丁基苯基)苯並三唑；分子內氫鍵；紫外光吸收；熱可塑性彈性體；拉電子官能基；密度泛函理論；紫外光吸收劑； Tinuvin PS ； H-bonding ； UV absorbent ； density functional theory

Abstract │ Reference (67) │ Altmetrics

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In this research, theoretical study with density functional theory (DFT) method were employed to calculate the absorb range and intensity of 2-(5’-tert-butyl-2’-hydroxylphenyl)benzotriazole and its derivatives first. And then use this starting material to synthesize  various derivatives such as 2-(5’-tert-butyl-2’-hydroxy-3’-nitrophenyl) benzotriazole(1), 2-(5’-tert-butyl-2’-methoxyphenyl)benzotriazole (2), 2- (3’-benzoyl-5’-tert-butyl-2’-hydroxyphenyl)benzotriazole (3),2-(3’-benze -nemethanol-2’-hydroxy-phenyl)benzotriazole (4), 2-(3’-benzenemethyl -5’-tertbutyl-2’-hydroxyphenyl)benzotriazole (5), 2-(5’-tert-butyl-2’- hydroxy-3’-methanolphenyl)benzotriazole (6), 2-(3’-aldehyde-5’-tert- butyl-2’-hydroxy-phenyl)benzotriazole (7), 2-[5’-tert-butyl-2’-hydroxy- 3’-(2’-naphthoyl)phenyl]benzotriazole (8), 2-[5’-tert-butyl-2’-hydroxy- 3’-(2’-naphthalenemethanol)phenyl]benzotriazole(9),2-[5’-tert-butyl-2’-hydroxy-3’-(2’-naphthoylmethyl)phenyl] benzotriazole (10). Each of the derivatives was dissolved in chloroform, respectively, to measure the UV absorption. Spectroscopic studues of UV absorption in solution state were also examined. According to the results of UV absorption, it was found compounds who has showed the intra-molecular hydrogen bonding and groups with  conjugation system connecting to the could increase the intensity of UV absorption. And it also found that electron withdrawing group connecting to C3 of the phenyl moiety could promote the intra-molecular hydrogen bonding. Compound (3) was add to Thermoplastic polyurethane to test the protection ability of UV, and the results show that it has great protection ability for UV-A.

Reference ( 67 ) 〈TOP〉

(4) United Nations Environment Programme Ozone Secretariat,2009.
連結：
(6) Philippe Autier1, Jean-François Doré, Eugène Schifflers, Jean-Pierre Cesarini4, Anne Bollaerts, Klaus F. Koelmel, Olaf Gefeller, André Liabeuf, Ferdy Lejeune, Danièle Lienard, Marie Joarlette1, Philippe Chemaly, Ulrich R. Kleeberg, Int. J. Cancer 1995, 61, 749
連結：
Choudhury b, R. Stephen Davidson, Journal of Photochemistry and Photobiology A: Chemistry. 95 (1996) 181 - 188
連結：
(10) Byoung-Hoo Lee, Hyun-Joong Kim. Polymer Degradation and Stability .91 (2006) 1025-1035
連結：
N.Serpone, Pure Appl. Chem. 71 (1999) 321.
連結：

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