Synthesis, Photophysical and Aggregation Properties of Novel Phenanthrene and Pyrene Substituted Phthalocyanines

Rangaraju Satish Kumar; Young-A Son

Korean Chemical Engineering Research, Vol.56, No.6, 792-797, December, 2018

DOI10.9713/kcer.2018.56.6.792 Export Citation

Synthesis, Photophysical and Aggregation Properties of Novel Phenanthrene and Pyrene Substituted Phthalocyanines

Rangaraju Satish Kumar, and Young-A Son^†

Department of Advanced Organic Materials Engineering, Chungnam National University, 99, Daehak-ro, Yuseong-gu, Daejeon, 34134, Korea

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We have explained the synthesis of novel phenanthrene and pyrene substituted phthalocyanines (PC-PHE and PC-PYR) and fully confirmed the structures by its spectral, photo physical and elemental analysis. For these phthalocyanines we checked the UV-Visible absorbance in PGMEA and chloroform and transmittance checked in PGMEA. The transmittance results suggested that these phthalocyanines are showing more than 90% transmittance at the 450-550 nm region. These synthesized molecules are nicely soluble in almost all industrial solvents. We checked the aggregation property of these phthalocyanines in PGMEA, and the results suggested no any aggregation for these molecules in PGMEA. The thermogravimetric analysis results concluded that PC-PHE and PC-PYR had high thermal stability. All studies explain that these new phthalocyanines are more suitable for LCD green color filter application.

Keywords:Phenanthrene;Aggregation;LCD;Tetrachlorophthalonitrile;PGMEA

[References]

Leznoff CC, Lever ABP, “Phthalocyanines: Properties and Applications,” VCH, New York, NY, USA, 1993.
Zagal JH, Coord. Chem. Rev., 119, 89 (1992)
Rosa MCD, Crutchley RJ, Coord. Chem. Rev., 233, 351 (2002)
Ng ACH, Li XY, Ng DKP, Macromolecules, 32(16), 5292 (1999)
Zhu B, Zhang X, Han M, Deng P, Li Q, J. Mol. Struct., 1079, 61 (2015)
Waltera MG, Rudineb AB, Wamser CC, J. Porphyrins Phthalocyanines, 14, 759 (2010)
Gursel YH, Senkal BF, Kandaz M, Yakuphanoglu F, Polyhedron, 28, 1490 (2009)
Karacaa H, Cayegil B, Sezer S, Synth. Met., 215, 134 (2016)
Basova TV, Mikhaleva NS, Hassan AK, Kiselev VG, Sens. Actuators B-Chem., 227, 634 (2016)
Lin D, Wang Y, Zhang Q, Zhou J, Zhou L, Wei S, J. Photochem. Photobiol. A-Chem., 315, 107 (2016)
Zorlu, Y., Dumoulin, F., Bouchu, D., Ahsen, V. and Lafont D, Tetrahedron Lett., 51, 6615 (2010)
Spadavecchia J, Ciccarella G, Siciliano P, Capone S, Rella R, Sens. Actuators B-Chem., 100, 88 (2004)
Elemans JAAW, Van Hameren R, Nolte RJM, Rowan AE, Adv. Mater., 18(10), 1251 (2006)
Cook P, Chambrier H, Academic Press, Amsterdam Vol. 19, pp. 105-150 (2003).
Forrest SR, Chem. Rev., 97(6), 1793 (1997)
Dieter W, Tsaryova O, Semioshkin A, Gabel D, Suvorova O, J. Organomet. Chem., 747, 98 (2013)
Guzel E, Atsay A, Nalbantoglu NS, Dogan L, Gul A, Kocak MB, Dyes Pigment., 97, 238 (2013)
Cook MJ, Dunn AJ, Howe SD, Thomson AJ, Harrison KJ, J. Chem. Soc.-Perkin Trans. 1, 1, 2453 (1988)
Makhseed S, Tuhl A, Samuel J, Zimcik P, Awadi NA, Novakova V, Dyes Pigment., 95, 351 (2012)
Leznoff CC, Lever ABP, Phthalocyanines: Properties and Applications, vol. 1. VCH: NewYork; vol. 4. 1996.
Ragoussi ME, Ince M, Torres T, Eur. J. Org. Chem., 29, 6475 (2013)
Jeong J, Kumar RS, Mergu N, Son YA, J. Mol. Struct., 1147, 649 (2017)
Ku KS, Kumar RS, Son YA, J. Nanosci. Nanotechnol., 18, 1716 (2017)
Jeong J, Kumar RS, Kim IJ, Son YA, Mol. Cryst. Liq. Cryst., 644(1), 249 (2017)
Garcia-Iglesias M, Yum JH, Humphry-Baker R, Zakeeruddin SM, Zechy M, Vazquez P, Palomares E, Gratzel M, Nazeeruddin MK, Torres T, Chem. Sci., 2, 1145 (2011)
Muthukumar P, Kim HS, Ku KS, Park JH, Son YA, Fibers Polym., 17, 553 (2016)
Durmus M, Ayhan MM, Gurek AG, Ahsen V, Dyes Pigment., 133, 311 (2016)
March J, “Advanced Organic Chemistry, Reactions, Mechanisms and Structure,” 3rd ed., Wiley, New York, pp. 853-933(1985).
Giribabu L, Vijay Kumar CH, Surendar A, Reddy VG, Chandrasekharam M, Reddy PY, Synth. Commun., 37, 4141 (2007)
Hoon Y, Chul KJ, Gun LB, Sanghun A, Pil HJ, Hun KS, Choi KJ, Namgoong JW, “High Transmissional Green Dye for LCD And Synthetic Method Thereof,” US20140114077A1 patent.
Choi J, Kim SH, Lee W, Yoon C, Kim JP, New J. Chem., 36, 812 (2012)
Sytnyk M, Glowacki ED, Yakunin S, Voss G, Schofberger W, Kriegner D, Stangl J, Trotta R, Gollner C, Tollabimazraehno S, Romanazzi G, Bozkurt Z, Havlicek M, Sariciftci NS, Heiss W, J. Am. Chem. Soc., 136(47), 16522 (2014)
Durmus M, Nyokong T, Polyhedron, 26, 2767 (2007)
Delman AD, Kelly JJ, Stein AA, Simms FB, Thermal Analysis, 2nd ed., 1 New York: Academic Press; p. 539(1969).

[1] Leznoff CC, Lever ABP, “Phthalocyanines: Properties and Applications,” VCH, New York, NY, USA, 1993.

[2] Zagal JH, Coord. Chem. Rev., 119, 89 (1992)

[3] Rosa MCD, Crutchley RJ, Coord. Chem. Rev., 233, 351 (2002)

[4] Ng ACH, Li XY, Ng DKP, Macromolecules, 32(16), 5292 (1999)

[5] Zhu B, Zhang X, Han M, Deng P, Li Q, J. Mol. Struct., 1079, 61 (2015)

[6] Waltera MG, Rudineb AB, Wamser CC, J. Porphyrins Phthalocyanines, 14, 759 (2010)

[7] Gursel YH, Senkal BF, Kandaz M, Yakuphanoglu F, Polyhedron, 28, 1490 (2009)

[8] Karacaa H, Cayegil B, Sezer S, Synth. Met., 215, 134 (2016)

[9] Basova TV, Mikhaleva NS, Hassan AK, Kiselev VG, Sens. Actuators B-Chem., 227, 634 (2016)

[10] Lin D, Wang Y, Zhang Q, Zhou J, Zhou L, Wei S, J. Photochem. Photobiol. A-Chem., 315, 107 (2016)

[11] Zorlu, Y., Dumoulin, F., Bouchu, D., Ahsen, V. and Lafont D, Tetrahedron Lett., 51, 6615 (2010)

[12] Spadavecchia J, Ciccarella G, Siciliano P, Capone S, Rella R, Sens. Actuators B-Chem., 100, 88 (2004)

[13] Elemans JAAW, Van Hameren R, Nolte RJM, Rowan AE, Adv. Mater., 18(10), 1251 (2006)

[14] Cook P, Chambrier H, Academic Press, Amsterdam Vol. 19, pp. 105-150 (2003).

[15] Forrest SR, Chem. Rev., 97(6), 1793 (1997)

[16] Dieter W, Tsaryova O, Semioshkin A, Gabel D, Suvorova O, J. Organomet. Chem., 747, 98 (2013)

[17] Guzel E, Atsay A, Nalbantoglu NS, Dogan L, Gul A, Kocak MB, Dyes Pigment., 97, 238 (2013)

[18] Cook MJ, Dunn AJ, Howe SD, Thomson AJ, Harrison KJ, J. Chem. Soc.-Perkin Trans. 1, 1, 2453 (1988)

[19] Makhseed S, Tuhl A, Samuel J, Zimcik P, Awadi NA, Novakova V, Dyes Pigment., 95, 351 (2012)

[20] Leznoff CC, Lever ABP, Phthalocyanines: Properties and Applications, vol. 1. VCH: NewYork; vol. 4. 1996.

[21] Ragoussi ME, Ince M, Torres T, Eur. J. Org. Chem., 29, 6475 (2013)

[22] Jeong J, Kumar RS, Mergu N, Son YA, J. Mol. Struct., 1147, 649 (2017)

[23] Ku KS, Kumar RS, Son YA, J. Nanosci. Nanotechnol., 18, 1716 (2017)

[24] Jeong J, Kumar RS, Kim IJ, Son YA, Mol. Cryst. Liq. Cryst., 644(1), 249 (2017)

[25] Garcia-Iglesias M, Yum JH, Humphry-Baker R, Zakeeruddin SM, Zechy M, Vazquez P, Palomares E, Gratzel M, Nazeeruddin MK, Torres T, Chem. Sci., 2, 1145 (2011)

[26] Muthukumar P, Kim HS, Ku KS, Park JH, Son YA, Fibers Polym., 17, 553 (2016)

[27] Durmus M, Ayhan MM, Gurek AG, Ahsen V, Dyes Pigment., 133, 311 (2016)

[28] March J, “Advanced Organic Chemistry, Reactions, Mechanisms and Structure,” 3rd ed., Wiley, New York, pp. 853-933(1985).

[29] Giribabu L, Vijay Kumar CH, Surendar A, Reddy VG, Chandrasekharam M, Reddy PY, Synth. Commun., 37, 4141 (2007)

[30] Hoon Y, Chul KJ, Gun LB, Sanghun A, Pil HJ, Hun KS, Choi KJ, Namgoong JW, “High Transmissional Green Dye for LCD And Synthetic Method Thereof,” US20140114077A1 patent.

[31] Choi J, Kim SH, Lee W, Yoon C, Kim JP, New J. Chem., 36, 812 (2012)

[32] Sytnyk M, Glowacki ED, Yakunin S, Voss G, Schofberger W, Kriegner D, Stangl J, Trotta R, Gollner C, Tollabimazraehno S, Romanazzi G, Bozkurt Z, Havlicek M, Sariciftci NS, Heiss W, J. Am. Chem. Soc., 136(47), 16522 (2014)

[33] Durmus M, Nyokong T, Polyhedron, 26, 2767 (2007)

[34] Delman AD, Kelly JJ, Stein AA, Simms FB, Thermal Analysis, 2nd ed., 1 New York: Academic Press; p. 539(1969).