Surfactant-Assisted Lateral Self-Assembly of One-Dimensional Supramolecular Aggregates of Lutetium Double-Decker Phthalocyaninates

Alexandra I. Zvyagina,^a Alena D. Naumova,^a Natalia V. Kuzmina,^a Alexander G. Martynov,^a Yulia G. Gorbunova,^b and Maria A. Kalinina^a@

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, RAS, 119071 Moscow, Russia

^bN.S. Kurnakov Institute of General and Inorganic Chemistry, RAS, 119991 Moscow, Russia

^@Corresponding author E-mail: kalinina@phyche.ac.ru

DOI: 10.6060/mhc210233k
Macroheterocycles 2021 14(1) 59-64

In memory of bright organic chemist and dedicated teacher of colorful beauty of life, Larisa Tomilova

The development of feasible strategies for integrating 1D organic semiconductors into films is a challenging issue for organic electronics exploiting planar architectures of microelectronic devices. Herein we describe the method of planar organization of 1D supramolecular aggregates assembled from lutetium crown-substituted double-decker phthalocyaninate into ordered ultrathin films. The method utilizes the Langmuir-Blodgett technique in combination with adding tert-butylamine during the synthesis of the supramolecular aggregates. The atomic force microscopy examination of the resulting films shows that the introduction of surfactant promotes spreading of hydrophobic aggregates on the water subphase yielding ordered ultrathin layers. The size of aggregates can be controlled by varying the ratio of the phthalocyanine ligands and surfactant in the system. The size of the aggregates increases with the concentration of the surfactant, whereas the morphology of the films evolves from a filamentary continuous structure to individual nanowires immobilized in the surfactant layer. The proposed strategy can be used to obtain ordered coatings from 1D aggregates from various organic discotics with semiconductor properties.

References:

Click here to expand or collapse this section

[1] Teng X., Chang B.-G., Wu K.-S. Sustainability 2021, 13, 1245-1261.
https://doi.org/10.3390/su13031245

[2] Huang Y., Hsiang E.-L., Deng M.-Y., Wu S.-T., Light Sci. Appl. 2020, 9, 105-121.
https://doi.org/10.1038/s41377-020-0341-9

[3] Gorbunova Y. G., Martynov A. G., Tsivadze A. Y. In: Handbook of Porphyrin Science, Vol. 24, World Scientific Publishing, 2012, p. 271-388.
https://doi.org/10.1142/9789814397605_0015

[4] Koifman O.I., Ageeva T.A., Beletskaya I.P., Averin A.D., Yakushev A.A., Tomilova L.G., Dubinina T.V., Tsivadze A.Y., Gorbunova Y.G., Martynov A.G., Konarev D.V., Khasanov S.S., Lyubovskaya R.N., Lomova T.N., Korolev V.V., Zenkevich E.I., Blaudeck T., von Borczyskowski C., Zahn D.R.T., Mironov A.F., Bragina N.A., Ezhov A.V., Zhdanova K.A., Stuzhin P.A., Pakhomov G.L., Rusakova N.V., Semenishyn N.N., Smola S.S., Parfenyuk V.I., Vashurin A.S., Makarov S.V., Dereven'kov I.A., Mamardashvili N.Z., Kurtikyan T.S., Martirosyan G.G., Burmistrov V.А., Aleksandriiskii V.V., Novikov I.V., Pritmov D.A., Grin M.A., Suvorov N.V., Tsigankov A.A., Fedorov A.Y., Kuzmina N.S., Nyuchev A.V., Otvagin V.F., Kustov A.V., Belykh D.V., Berezin D.B., Solovieva A.B., Timashev P.S., Milaeva E.R., Gracheva Y.A., Dodokhova M.A., Safronenko A.V., Shpakovsky D.B., Syrbu S.A., Gubarev Y.A., Kiselev A.N., Koifman M.O., Lebedeva N.S., Yurina E.S. Macroheterocycles 2020, 13, 311-467.
https://doi.org/10.6060/mhc200814k

[5] Zeis R., Siegrist T., Kloc C. Appl. Phys. Lett. 2005, 86, 022103.
https://doi.org/10.1063/1.1849438

[6] Jiang H., Ye J., Hu P., Wei F., Du K., Wang N., Ba T., Feng S., Kloc C. Sci. Rep. 2015, 4, 7573.
https://doi.org/10.1038/srep07573

[7] Pushkarev V.E., Tolbin A.Y., Zhurkin F.E., Borisova N.E., Trashin S.A., Tomilova L.G., Zefirov N.S. Chem. - A Eur. J. 2012, 18, 9046-9055.
https://doi.org/10.1002/chem.201200361

[8] Turek P., Petit P., Andre J.J., Simon J., Even R., Boudjema B., Guillaud G., Maitrot M. J. Am. Chem. Soc. 1987, 109, 5119-5122.
https://doi.org/10.1021/ja00251a012

[9] Bassoul P., Toupance T., Simon J., Sensors Actuators B Chem. 1995, 26, 150-152.
https://doi.org/10.1016/0925-4005(94)01576-4

[10] Toupance T., Benoit H., Sarazin D., Simon J. J. Am. Chem. Soc. 1997, 119, 9191-9197.
https://doi.org/10.1021/ja9644438

[11] Martynov A.G., Gorbunova Y.G., Tsivadze A.Y. Prot. Met. Phys. Chem. Surfaces 2011, 47, 465-470.
https://doi.org/10.1134/S2070205111040125

[12] Martynov A. G., Polovkova M. A., Berezhnoy G. S., Sinelshchikova A. A., Dolgushin F. M., Birin K. P., Kirakosyan G. A., Gorbunova Y.G., Tsivadze A.Y. Inorg. Chem. 2020, 59, 9424-9433.
https://doi.org/10.1021/acs.inorgchem.0c01346

[13] Toupance T., Ahsen V., Simon J. J. Am. Chem. Soc. 1994, 116, 5352-5361.
https://doi.org/10.1021/ja00091a046

[14] Iyechika B.Y.Y., Yakushi K., Ikemoto I., Kuroda H. Acta Cryst 1982, B38, 766-770.
https://doi.org/10.1107/S056774088200404X

[15] Ukei K. Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 1973, 29, 2290-2292.
https://doi.org/10.1107/S0567740873006497

[16] Otsuki J., Kawaguchi S., Yamakawa T., Asakawa M., Miyake K. Langmuir 2006, 22, 5708-5715.
https://doi.org/10.1021/la0608617

[17] Auwärter W., Écija D., Klappenberger F., Barth J.V. Nat. Chem. 2015, 7, 105-120.
https://doi.org/10.1038/nchem.2159

[18] Hussain S. A., Dey B., Bhattacharjee D., Mehta N. Heliyon 2018, 4, e01038.
https://doi.org/10.1016/j.heliyon.2018.e01038

[19] Zvyagina A.I., Meshkov I.N., Ezhov A.A., Shiryaev A., Gorbunova Y.G., Birin K.P., Tsivadze A.Y., Arslanov V.V, Kalinina M.A. Colloids Surfaces A Physicochem. Eng. Asp. 2016, 509, 376-383.
https://doi.org/10.1016/j.colsurfa.2016.09.046

[20] Zhang R., Li B., Iovu M. C., Jeffries-EL M., Sauvé G., Cooper J., Jia S., Tristram-Nagle S., Smilgies D.M., Lambeth D.N., McCullough R.D., Kowalewski T. J. Am. Chem. Soc. 2006, 128, 3480-3481.
https://doi.org/10.1021/ja055192i

[21] Sauvé G., McCullough R.D. Adv. Mater. 2007, 19, 1822-1825.
https://doi.org/10.1002/adma.200602368

[22] Klauk H., Halik M., Zschieschang U., Schmid G., Radlik W., Weber W. J. Appl. Phys. 2002, 92, 5259-5263.
https://doi.org/10.1063/1.1511826

[23] Niles E.T., Roehling J.D., Yamagata H., Wise A.J., Spano F.C., Moulé A.J., Grey J.K. J. Phys. Chem. Lett. 2012, 3, 259-263.
https://doi.org/10.1021/jz201509h

[24] Teo W.E., Ramakrishna S. Nanotechnology 2006, 17, R89-R106.
https://doi.org/10.1088/0957-4484/17/14/R01

[25] Son M., Park K.H., Shao C., Würthner F., Kim D. J. Phys. Chem. Lett. 2014, 5, 3601-3607.
https://doi.org/10.1021/jz501953a

[26] Pan L., Qiu H., Dou C., Li Y., Pu L., Xu J., Shi Y. Int. J. Mol. Sci. 2010, 11, 2636-2657.
https://doi.org/10.3390/ijms11072636

[27] Wang P., Li Z., Zhang L., Tong L. Opt. Lett. 2013, 38, 1040-1042.
https://doi.org/10.1364/OL.38.001040

[28] Laza S. C., Polo M., Neves A. A. R., Cingolani R., Camposeo A., Pisignano D., Adv. Mater. 2012, 24, 1304-1308.
https://doi.org/10.1002/adma.201103357

[29] Palacin S., Ruaudel-Teixier A., Barraud A., J. Phys. Chem. 1989, 93, 7195-7199.
https://doi.org/10.1021/j100357a034

[30] Palacin S., Lesieur P., Stefanelli I., Barraud A., Thin Solid Films 1988, 159, 83-90.
https://doi.org/10.1016/0040-6090(88)90619-0

[31] Gregory B. W., Vaknin D., Gray J. D., Ocko B. M., Stroeve P., Cotton T. M., Struve W. S., J. Phys. Chem. B 1997, 101, 2006-2019.
https://doi.org/10.1021/jp963152i

[32] Pang M., Cairns A. J., Liu Y., Belmabkhout Y., Zeng H. C., Eddaoudi M. J. Am. Chem. Soc. 2013, 135, 10234-10237.
https://doi.org/10.1021/ja403994u

[33] Martynov A.G., Berezhnoy G.S., Safonova E.A., Polovkova M.A., Gorbunova Y.G., Tsivadze A.Y. Macroheterocycles 2019, 12, 75-81.
https://doi.org/10.6060/mhc181225m

[34] Toupance T., Ahsen V., Simon J. J. Chem. Soc. Chem. Commun. 1994, 1, 75-76.
https://doi.org/10.1039/c39940000075

[35] Selektor S.L., Shokurov A.V., Raitman O.A., Sheinina L.S., Arslanov V.V., Birin K.P., Gorbunova Y.G., Tsivadze A.Y. Colloid J. 2012, 74, 334-345.
https://doi.org/10.1134/S1061933X12020111

Attachment	Size
mhc210233k.pdf	1.27 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Surfactant-Assisted Lateral Self-Assembly of One-Dimensional Supramolecular Aggregates of Lutetium Double-Decker Phthalocyaninates

References: