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Molecular-scale STM observations clearly revealed that 2-PyzS SAMs at pH 2 had a short-range ordered phase of (2\u221a3 \u00d7 \u221a21)R30\u00b0 structure with a standing-up adsorption structure. However, 2-PyzS SAMs at pH 8 had a very unique long-range ordered phase, showing a \u201cladder-like molecular arrangement\u201d with bright repeating rows. This ordered phase was assigned to the (3 \u00d7 \u221a37)R43\u00b0 structure, consisting of two different adsorption structures: standing-up and tilted adsorption structures. The average arial density of 2-PyzS SAMs on Au(111) at pH 8 was calculated to be 49.47 \u00c52\/molecule, which is 1.52 times more loosely packed compared to the SAMs at pH 2 with 32.55 \u00c52\/molecule. XPS measurements showed that 2-PyzS SAMs at pH 2 and pH 8 were mainly formed through chemical interactions between the sulfur anchoring group and the Au(111) substrates. The proposed structural models of packing structures for 2-PyzS SAMs on Au(111) at different pHs are well supported by the XPS results. The results of this study will provide new insights into the formation, surface structure, and molecular orientation of SAMs by N-heteroaromatic thiols with pyrazine molecular backbone on Au(111) at the molecular level.<\/jats:p>","DOI":"10.3390\/ijms26010160","type":"journal-article","created":{"date-parts":[[2024,12,31]],"date-time":"2024-12-31T07:34:19Z","timestamp":1735630459000},"page":"160","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Formation and Surface Structures of Long-Range Ordered Self-Assembled Monolayers of 2-Mercaptopyrazine on Au(111)"],"prefix":"10.3390","volume":"26","author":[{"given":"Dongjin","family":"Seo","sequence":"first","affiliation":[{"name":"Department of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jin Wook","family":"Han","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongki","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yeon O","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hyun Sun","family":"Sung","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Riko","family":"Kaizu","sequence":"additional","affiliation":[{"name":"Department of Materials Science and Engineering, School of Materials and Chemical Technology, Institute of Science Tokyo, Yokohama 226-8502, Kanagawa, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-3839-546X","authenticated-orcid":false,"given":"Glenn Villena","family":"Latag","sequence":"additional","affiliation":[{"name":"Department of Materials Science and Engineering, School of Materials and Chemical Technology, Institute of Science Tokyo, Yokohama 226-8502, Kanagawa, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4065-1807","authenticated-orcid":false,"given":"Tomohiro","family":"Hayashi","sequence":"additional","affiliation":[{"name":"Department of Materials Science and Engineering, School of Materials and Chemical Technology, Institute of Science Tokyo, Yokohama 226-8502, Kanagawa, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3404-2300","authenticated-orcid":false,"given":"Nam-Suk","family":"Lee","sequence":"additional","affiliation":[{"name":"National Institute for Nanomaterials Technology, Pohang University of Science and Technology, 77 Cheongam-ro, Nam-gu, Pohang 37673, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6115-7971","authenticated-orcid":false,"given":"Jaegeun","family":"Noh","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Republic of Korea"},{"name":"Research Institute for Convergence of Basic Science, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1103","DOI":"10.1021\/cr0300789","article-title":"Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology","volume":"105","author":"Love","year":"2005","journal-title":"Chem. 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