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The synthesis, structure, spectroscopic and electrochemical properties of two such\n                    <jats:italic>carbo<\/jats:italic>\n                    \u2010stilbenes are described at complementary experimental and computational DFT levels. In the selected targets, the bare skeletal\n                    <jats:italic>carb<\/jats:italic>\n                    o\u2010mer of\n                    <jats:italic>carbo<\/jats:italic>\n                    \u2010stilbene is decorated by 8 or 10 phenyl groups, 0 or 2\n                    <jats:italic>tert<\/jats:italic>\n                    \u2010butyl groups, and 2\n                    <jats:italic>n<\/jats:italic>\n                    \u2010octyl chains, the later substituents being introduced to compensate anticipated solubility issues. As in the parent stilbene series, isomers of the phenylated\n                    <jats:italic>carbo<\/jats:italic>\n                    \u2010stilbenes are characterized. The\n                    <jats:italic>cis\u2010<\/jats:italic>\n                    and\n                    <jats:italic>trans\u2010<\/jats:italic>\n                    isomers are, however, formed in almost equal amounts and could not be separated by either chromatography or crystallization. Nevertheless, due to a slow interconversion at the NMR time scale (up to 55\u2009\u00b0C) the\n                    <jats:sup>1<\/jats:sup>\n                    H NMR signals of both isomers of the two\n                    <jats:italic>carbo<\/jats:italic>\n                    \u2010stilbenes could be tentatively assigned. The calculated structure of the\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010isomer exhibits a helical shape, consistent with the observed magnetic shielding of phenyl\n                    <jats:italic>p<\/jats:italic>\n                    \u2010C\n                    <jats:italic>H<\/jats:italic>\n                    nuclei residing inside the shielding cone of the facing C\n                    <jats:sub>18<\/jats:sub>\n                    ring. The presence of the two isomers in solution also gives rise to quite broad UV\u2010vis absorption spectra with main bands at\n                    <jats:italic>ca<\/jats:italic>\n                    460, 560 and 710\u2005nm, and a significant bathochromic shift for the decaphenylated\n                    <jats:italic>carbo<\/jats:italic>\n                    \u2010stilbene\n                    <jats:italic>vs<\/jats:italic>\n                    the di\u2010\n                    <jats:italic>tert<\/jats:italic>\n                    \u2010butyl\u2010octaphenylated counterpart. Square wave voltammograms do not show any resolution of the two isomers, giving a reversible reduction wave at \u22120.65 or \u22120.58\u2005V\/SCE, and an irreversible oxidation peak at 1.11\u2005V\/SCE, those values being classical for most\n                    <jats:italic>carbo<\/jats:italic>\n                    \u2010benzene derivatives. Calculated NICS values (NICS(1)=\u221212.5\u00b10.2\u2005ppm) also indicate that the aromatic nature of the C\n                    <jats:sub>18<\/jats:sub>\n                    rings is not markedly affected by the dialkynylbutatriene (DAB) connector between them.\n                  <\/jats:p>","DOI":"10.1002\/chem.202400451","type":"journal-article","created":{"date-parts":[[2024,2,26]],"date-time":"2024-02-26T08:36:00Z","timestamp":1708936560000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["From Stilbenes to\n                    <i>carbo<\/i>\n                    \u2010Stilbenes: an Encouraging Prospect"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1419-3419","authenticated-orcid":false,"given":"Chongwei","family":"Zhu","sequence":"first","affiliation":[{"name":"Facult\u00e9 Science et Ing\u00e9nierie - D\u00e9partement de Chimie. Unsaturated molecules for physics, biology and chemistry group. Universit\u00e9 Toulouse III - Paul Sabatier  118 route de Narbonne 31-062 Toulouse Cedex 09 France"},{"name":"Key Laboratory of Functional Molecular Solids Ministry of Education and School of Chemistry and Materials Science Anhui Normal University  Wuhu 241002 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alix","family":"Saquet","sequence":"additional","affiliation":[{"name":"LCC\u2013CNRS Universit\u00e9 de Toulouse  CNRS, UPS Toulouse France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0900-7332","authenticated-orcid":false,"given":"Val\u00e9rie","family":"Maraval","sequence":"additional","affiliation":[{"name":"LCC\u2013CNRS Universit\u00e9 de Toulouse  CNRS, UPS Toulouse France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3989-3021","authenticated-orcid":false,"given":"Christian","family":"Bijani","sequence":"additional","affiliation":[{"name":"LCC\u2013CNRS Universit\u00e9 de Toulouse  CNRS, UPS Toulouse France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5759-766X","authenticated-orcid":false,"given":"Xiuling","family":"Cui","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Molecular Medicine of Ministry of Education Key Laboratory of Fujian Molecular Medicine Key Laboratory of Xiamen Marine and Gene Drugs School of Biomedical Sciences Huaqiao University  Xiamen 361021 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8997-2599","authenticated-orcid":false,"given":"Albert","family":"Poater","sequence":"additional","affiliation":[{"name":"Institut de Qu\u00edmica Computacional i Cat\u00e0lisi, Departament de Qu\u00edmica Universitat de Girona, c\/ M\u00aa Aur\u00e8lia  Capmany 69 17003 Girona Catalonia Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4491-6390","authenticated-orcid":false,"given":"Remi","family":"Chauvin","sequence":"additional","affiliation":[{"name":"Facult\u00e9 Science et Ing\u00e9nierie - D\u00e9partement de Chimie. Unsaturated molecules for physics, biology and chemistry group. Universit\u00e9 Toulouse III - Paul Sabatier  118 route de Narbonne 31-062 Toulouse Cedex 09 France"},{"name":"Engineering Research Center of Molecular Medicine of Ministry of Education Key Laboratory of Fujian Molecular Medicine Key Laboratory of Xiamen Marine and Gene Drugs School of Biomedical Sciences Huaqiao University  Xiamen 361021 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,3,13]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"Fore recent reviews on stilbene derivatives see:"},{"key":"e_1_2_7_2_2","volume-title":"Stilbenes: Applications in Chemistry, Life Sciences and Materials Science"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.7b00089"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202001031"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2OB01982E"},{"key":"e_1_2_7_6_1","unstructured":"See for example:"},{"key":"e_1_2_7_7_2","unstructured":"ref [1a] pp. 189\u2013223;"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.toxlet.2015.05.001"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867323666160517121629"},{"key":"e_1_2_7_10_2","first-page":"3225","volume":"39","author":"Wahedi H. M.","year":"2021","journal-title":"J. Biomol. Struct. Dyn."},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11418-023-01727-5"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.3390\/plants12162935"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules28114482"},{"key":"e_1_2_7_14_1","unstructured":"See for example:"},{"key":"e_1_2_7_15_2","unstructured":"ref [1a] pp. 159\u2013188;"},{"key":"e_1_2_7_16_2","first-page":"9597","volume":"5","author":"Cao M.","year":"2017","journal-title":"J. Phys. Chem. 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