프탈로시아닌계 하이브리드 유도체들의 합성 및 이의 특성에 관한 연구

김성진; 안바룡; 이근대; 박성수; Seong Jin Kim; Ba Ryong An; Gun-Dae Lee; Seong Soo Park

Applied Chemistry for Engineering, Vol.24, No.3, 266-273, June, 2013

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프탈로시아닌계 하이브리드 유도체들의 합성 및 이의 특성에 관한 연구

The Syntheses of Phthalocyanine Hybrid Derivatives and Their Properties

김성진, 안바룡, 이근대 , 박성수 ^†

부경대학교 공업화학과

Seong Jin Kim, Ba Ryong An, Gun-Dae Lee , and Seong Soo Park^†

Department of Industrial & Engineering Chemistry, Pukyoung National University, Busan 608-739, Korea

E-mail:

초록

프탈로시아닌, 포르피린, 서브프탈로시아닌 및 퍼릴렌 화합물들은 광저장매체, 유기 태양전지, LCD, PDP, 반도체, 위폐감별용 재료 등으로 응용된다. 본 연구에서는 퍼릴렌, 서브프탈로시아닌 및 포르피린을 프탈로시아닌 프레임에 가교 결합시켜서 프탈로시아닌계 하이브리드 유도체를 합성하였다. 합성된 하이브리드 시료들은 두 가지 다른 파장영역을 동시에 흡수하였다. 또한, 프탈로시아닌에 비하여 유도체의 도입으로 인하여 시료의 용해도가 향상되었으며, 치환된 유도체의 종류에 따라 Q-band가 장파장 영역으로 이동하는 정도가 상이하였다. 시료들의 화학적 특성 및 광학적 특성은 FT-IR, 1H-NMR, UV-Vis를 이용하여 비교ㆍ분석하였다.

Phthalocyanine (Pc), porphyrin, subphthalocyanine, and perylene compounds can be applicable to the fields of optical storage media, organic solar cell, LCD, PDP, semiconductor, and counterfeit money detection etc. In this study, phthalocyanine hybrid derivatives were synthesized by cross-linking perylene, subphthalocyanine, or porphyrin to the main frame of Pc. Absorbtion band of two different wavelengths appeared simultaneously in the phthalocyanine hybrid derivatives. Compared to phthalocyanine, the solubility was enhanced and the degree of Q-band shift was changed according to the kind of substitute compounds. The chemical and optical properties of samples were analyzed using FT-IR, 1H-NMR, and UV-Vis spectroscopic techniques.

Keywords:phthalocyanine;subphthalocyanine;porphyrin;hybrid;solubility

[References]

Leznoff CC, Phthalocyanine; Properties and Applications, Lever ABP (Eds.), VCH-Publishers, New York, 219 (1996)
Dini D, Barthel M, Hanack M, Eur. J. Org. Chem., 20, 3759 (2001)
Kadish KM, Smith KM, The Porphyrin Handbook, Guilard R (Eds.), Academic Press, San Diego, 1 (2003)
Kasuga K, Fujita A, Miyazako T, Handa M, Sugimori T, Inorg. Chem. Commun., 3, 634 (2000)
Frampton CS, O’Conner JM, Retevson J, Silver J, Displays., 174 (1988)
Gurek A, Ahsen V, Gul A, Bekaroglu O, J. Chem. Soc.Dalton Trans., 3367 (1991)
Hjelm J, Handel RW, Hagfeldt A, Constable EC, Housecroft CE, Forster RJ, Inorg. Chem., 44(4), 1073 (2005)
Seybold G, Wagenblast G, Dyes and Pigments., 11, 303 (1989)
Dotcheva D, Klapper M, Mullen K, Macromol. Chem. Phys., 195, 1905 (1994)
Rohr Y, Schlichting P, Btihm A, Cross M, Meerholz K, Briuchle C, Mtiilen K, Angew. Chem., Int. Ed. Engl., 37, 1434 (1988)
Volkov KA, Avramenko GV, Negrimovskii VM, Luk’yanets EA, Zh. Obshch. Khim., 77, 1022 (2007)
Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J, Korsakoff L, J. Org. Chem., 32, 476 (1967)
George RD, Snow AW, J. Heterocyclic Chem., 32, 495 (1995)
Young JG, Onyebuagu W, J. Org. Chem., 55, 2155 (1990)
Thomas DW, Martell AR, J. Am. Chem. Soc., 78, 1338 (1956)
Claessens CG, Gonzalez-Rodriguez D, Torres T, Chem. Rev., 102(3), 835 (2002)
Qiu T, Xu X, Liu J, Qian X, Dyes & Pigments., 83, 127 (2009)

[Related Articles]

[1] Leznoff CC, Phthalocyanine; Properties and Applications, Lever ABP (Eds.), VCH-Publishers, New York, 219 (1996)

[2] Dini D, Barthel M, Hanack M, Eur. J. Org. Chem., 20, 3759 (2001)

[3] Kadish KM, Smith KM, The Porphyrin Handbook, Guilard R (Eds.), Academic Press, San Diego, 1 (2003)

[4] Kasuga K, Fujita A, Miyazako T, Handa M, Sugimori T, Inorg. Chem. Commun., 3, 634 (2000)

[5] Frampton CS, O’Conner JM, Retevson J, Silver J, Displays., 174 (1988)

[6] Gurek A, Ahsen V, Gul A, Bekaroglu O, J. Chem. Soc.Dalton Trans., 3367 (1991)

[7] Hjelm J, Handel RW, Hagfeldt A, Constable EC, Housecroft CE, Forster RJ, Inorg. Chem., 44(4), 1073 (2005)

[8] Seybold G, Wagenblast G, Dyes and Pigments., 11, 303 (1989)

[9] Dotcheva D, Klapper M, Mullen K, Macromol. Chem. Phys., 195, 1905 (1994)

[10] Rohr Y, Schlichting P, Btihm A, Cross M, Meerholz K, Briuchle C, Mtiilen K, Angew. Chem., Int. Ed. Engl., 37, 1434 (1988)

[11] Volkov KA, Avramenko GV, Negrimovskii VM, Luk’yanets EA, Zh. Obshch. Khim., 77, 1022 (2007)

[12] Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J, Korsakoff L, J. Org. Chem., 32, 476 (1967)

[13] George RD, Snow AW, J. Heterocyclic Chem., 32, 495 (1995)

[14] Young JG, Onyebuagu W, J. Org. Chem., 55, 2155 (1990)

[15] Thomas DW, Martell AR, J. Am. Chem. Soc., 78, 1338 (1956)

[16] Claessens CG, Gonzalez-Rodriguez D, Torres T, Chem. Rev., 102(3), 835 (2002)

[17] Qiu T, Xu X, Liu J, Qian X, Dyes & Pigments., 83, 127 (2009)