Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain length

作者: Lydia X. Sosa-Vargas , Isabelle Chambrier , Colin J. MacDonald , Simon J. Coles , Graham J. Tizzard

DOI: 10.1142/S108842461350020X

关键词:

摘要: The preparation of some peripherally substituted (2,3,9,10,16,17,23,24) and non-peripherally (1,4,8,11,15,18,22,25) octaalkyl lead(II) phthalocyanines with different alkyl chain lengths (6, 7, 8 or 9 carbons) is described a comparison their properties reported. X-ray structure analyses the isomeric peripheral non-peripheral octakis(octyl)phthalocyaninato compounds reveal greater degree distortion ligand ring system from planarity in former derivative. series exhibit columnar liquid crystal behavior whereas isomers do not. lability lead ion was investigated using 1H NMR spectrometry under specific set conditions (8.8 × 10-4 M solutions phthalocyanine d8-toluene containing d4-acetic acid 2.06 10-5 M). All underwent catalyzed demetalation at rates dependent upon location substituents and, more surprisingly, length groups. Under these within each labile than that isomer.

参考文章(37)
Gwynn P. Ellis, Trevor M. Romney-Alexander, Cyanation of aromatic halides Chemical Reviews. ,vol. 87, pp. 779- 794 ,(1987) , 10.1021/CR00080A006
P. Weber, D. Guillon, A. Skoulios, Antiferroelectric stacking in lead phthalocyanine columnar mesophases The Journal of Physical Chemistry. ,vol. 91, pp. 2242- 2243 ,(1987) , 10.1021/J100293A007
Y. Sadaoka, T.A. Jones, W. Göpel, Fast NO2 detection at room temperature with optimized lead phthalocyanine thin-film structures Sensors and Actuators B: Chemical. ,vol. 1, pp. 148- 153 ,(1990) , 10.1016/0925-4005(90)80191-2
Christian Piechocki, Jacques Simon, Antoine Skoulios, Daniel Guillon, Patrick Weber, Annelides. 7. Discotic mesophases obtained from substituted metallophthalocyanines. Toward liquid crystalline one-dimensional conductors Journal of the American Chemical Society. ,vol. 104, pp. 5245- 5247 ,(1982) , 10.1021/JA00383A050
Larissa A Valkova, Sergei V Zyablov, Victor V Erokhin, Oscar I Koifman, None, Nanoaggregates in floating layers of azaporphyrins Journal of Porphyrins and Phthalocyanines. ,vol. 14, pp. 513- 522 ,(2010) , 10.1142/S1088424610002380
K.F. Schoch, T.A. Temofonte, IR response of phthalocyanine thin films to nitrogen dioxide Thin Solid Films. ,vol. 165, pp. 83- 89 ,(1988) , 10.1016/0040-6090(88)90681-5
R.A. Collins, K.R. Strickland, M.J. Jeffery, K. Davidson, T.A. Jones, The effects of impurities on the microtopography of lead phthalocyanine thin films Materials Letters. ,vol. 10, pp. 170- 174 ,(1990) , 10.1016/0167-577X(90)90083-X
Biswanath Mukherjee, Asim K. Ray, Ashwani K. Sharma, Michael J. Cook, Isabelle Chambrier, A simply constructed lead phthalocyanine memory diode Journal of Applied Physics. ,vol. 103, pp. 074507- ,(2008) , 10.1063/1.2903061
S.M. O’Flaherty, S.V. Hold, M.J. Cook, T. Torres, Y. Chen, M. Hanack, W.J. Blau, Molecular Engineering of Peripherally And Axially Modified Phthalocyanines for Optical Limiting and Nonlinear Optics Advanced Materials. ,vol. 15, pp. 19- 32 ,(2003) , 10.1002/ADMA.200390002
Tsuyoshi Muto, Tetsuji Temma, Mutsumi Kimura, Kenji Hanabusa, Hirofusa Shirai, A new phthalocyanine derivative having peripheral 2-thienyl substituents Chemical Communications. pp. 1649- 1650 ,(2000) , 10.1039/B004694I