Abstract
The direct polymerization via irreversible C-C coupling on inert substrates will give access to new low-dimensional advanced functional materials and simplify their industrial fabrication. In this work, we present our initial results in the application of Glaser coupling to the direct on-surface polymerization of a model diacetylene compound at the solid-vapor interface. The self-assembly of the monomer and polymerization products was characterized using scanning tunneling microscopy (STM). In addition, selected optical properties and the electronic structure of all compounds were investigated.
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Novoselov K. S., Fal’ko V. I., Colombo L., Gellert P. R., Schwab M. G., Kim K., Nature, 2012, 490, 192
Tan C., Cao X., Wu X. J., He Q., Yang J., Zhang X., Chen J., Zhao W., Han S., Nam G. H., Sindoro M., Zhang H., Chem. Rev., 2017, 117, 6225
Xu M. S., Liang T., Shi M. M., Chen H. Z., Chem. Rev., 2013, 113, 3766
Yeo J., Jung G. S., Martin-Martinez F. J., Beem J., Qin Z., Buehler M. J., Adv. Mater., 2019, 31, 1805665
Xie C. P., Wang N., Li X. F., Xu G. R., Huang C. S., Chem. Eur. J., 2020, 26, 569
Gao X., Liu H. B., Wang D., Zhang J., Chem. Soc. Rev., 2019, 48, 908
Glaser C., Justus Liebigs Ann. Chem., 1870, 154, 137
Du R., Zhang N., Xu H., Mao N., Duan W., Wang J., Zhao Q., Liu Z., Zhang J., Adv. Mater., 2014, 26, 8053
Allendorf M. D., Dong R. H., Feng X. L., Kaskel S., Matoga D., Stavila V., Chem. Rev., 2020, 120, 8581
Zhang T., Hou Y., Dzhagan V., Liao Z., Chai G., Loeffler M., Olianas D., Milani A., Xu S., Tommasini M., Zahn D. R. T., Zheng Z., Zschech E., Jordan R., Feng X., Nat. Commun., 2018, 9, 1140
Li X. C., Zhang H. M., Chi L. F., Adv. Mater., 2019, 31, 1804087
Gao H.-Y., Zhong D., Mönig H., Wagner H., Held P.-A., Timmer A., Studer A., Fuchs H., J. Phys. Chem. C, 2014, 118, 6272
Sun Q., Cai L., Ma H., Yuan C., Xu W., ACS Nano, 2016, 10, 7023
Zhang Y.-Q., Kepcija N., Kleinschrodt M., Diller K., Fischer S., Papageorgiou A. C., Allegretti F., Bjork J., Klyatskaya S., Klappenberger F., Ruben M., Barth J. V., Nat. Commun., 2012, 3, 1286
Yue J. Y., Fan W., Chen T., Wang Z. H., Wang D., Wan L. J., Chem. Asian J., 2020, 15, 2627
Sun K. W., Fang Y., Chi L. F., ACS Materials Letters, 2021, 3, 56
Colazzo L., Sedona F., Moretto A., Casarin M., Sambi M., J. Am. Chem. Soc., 2016, 138, 10151
Horcas I., Fernandez R., Gomez-Rodriguez J. M., Colchero J., Gomez-Herrero J., Baro A. M., Rev. Sci. Instrum, 2007, 78, 013705
te Velde G., Bickelhaupt F. M., Baerends E. J., Fonseca Guerra C., van Gisbergen S. J. A., Snijders J. G., Ziegler T., Journal of Computational Chemistry, 2001, 22, 931
Nagaoka M., Tsurumaki E., Nishiuchi M., Iwanaga T., Toyota S., J. Org. Chem., 2018, 83, 5784
Taylor M. S., Swager T. M., Angew. Chem. Int. Ed., 2007, 46, 8480
Krukau A. V., Vydrov O. A., Izmaylov A. F., Scuseria G. E., the Journal of Chemical Physics, 2006, 125, 224106
Wang C. C., Gao Y., Shreve A. P., Zhong C., Wang L., Mudalige K., Wang H. L., Cotlet M., J. Phys. Chem. B, 2009, 113, 16110
Leclère P., Surin M., Viville P., Lazzaroni R., Kilbinger A. F. M., Henze O., Feast W. J., Cavallini M., Biscarini F., Schenning A. P. H. J., Meijer E. W., Chem. Mater., 2004, 16, 4452
Acknowledgements
This work was supported by the Natural Sciences and Engineering Research Council of Canada(NSERC) Discovery Grants, the National Natural Science Foundation of China(No.22102110), the Natural Science Foundation of Jiangsu Province, China(No.SBK2021040457) and the NSERC Scholarship(No.PDF-532834-2019).
CUCCIA Louis A. acknowledges NSERC and FQRNT and the multi-institutional Québec Center for Advanced Materials (QCAM) for financial support of this research.
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Fang, Y., Heydari, Z., Liu, C. et al. Glaser Coupling of Substituted Anthracene Diynes on a Non-metallic Surface at the Vapor-Solid Interface. Chem. Res. Chin. Univ. 37, 1143–1148 (2021). https://doi.org/10.1007/s40242-021-1324-y
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DOI: https://doi.org/10.1007/s40242-021-1324-y