Optical properties and aggregation of novel azo-dyes bearing an end-capped oligo(ethylene glycol) side chain in solution,solid state and Langmuir–Blodgett films |
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| Affiliation: | 1. Instituto de Investigaciones en Materiales UNAM, Circuito Exterior Ciudad Universitaria C.P. 04510, México D.F. México;2. Instituto de Ciencias Nucleares UNAM, Circuito Exterior Ciudad Universitaria C.P. 04510, México D.F. México;1. Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan;2. Department of Materials Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan;1. Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry, University of Science and Technology Beijing, Beijing 100083, China;2. College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, China;1. Department of Chemistry, Payame Noor University, Abhar, Zanjan, Islamic Republic of Iran;2. Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Islamic Republic of Iran |
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| Abstract: | Optical properties and aggregation of two novel azo-dyes N-methyl-N-{4-[(E)-(4-nitrophenyl)diazenyl]phenyl}-N-(3,6,9-trioxadecas-1-yl)amine (RED-PEGM-3) and N-methyl-N-{4-[(E)-(4-nitrophenyl)diazenyl] phenyl}-N-(3,6,9,12,15,18,21,24-octaoxapentaeicos-1-yl)amine (RED-PEGM-8) were studied by UV–vis spectroscopy in solution, solid state and Langmuir–Blodgett films. The results were compared to those obtained for their precursor 1-amino-4′-nitroazobenzene (Disperse Orange 3, DO3) and 1-N-methylamino-4′-nitroazobenzene (RED-H). Increasing the polarity of methanol:water mixtures gave rise to the formation of H-aggregates for all dyes. Similar aggregates were also detected in cast films. NOESY, 2D 1H NMR experiments carried out in aqueous solutions of RED-PEGM-8 revealed the formation of atypical antiparallel H-aggregates. Only RED-PEGM-3 gave traces of J-aggregates in the solid state. RED-PEGM-3 and RED-PEGM-8 readily form J-aggregates in Y-type Langmuir–Blodgett films. |
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