{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T13:43:04Z","timestamp":1760362984309,"version":"build-2065373602"},"reference-count":41,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2020,5,5]],"date-time":"2020-05-05T00:00:00Z","timestamp":1588636800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["2018\/00106-7, 2013\/07276-1, 2012\/24092-9"],"award-info":[{"award-number":["2018\/00106-7, 2013\/07276-1, 2012\/24092-9"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["407990\/2018-6 , 303890\/2019-3"],"award-info":[{"award-number":["407990\/2018-6 , 303890\/2019-3"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The synthesis of the new dye 1,6-methano[10]annulenecyanine is described. For this purpose, the 3,4-dicyano-1,6-methano[10]annulene and 3,4-carboxyimide-1,6-methano[10]annulene buildings blocks were synthesized in six to eight steps. In both cases, these building blocks were then cyclotetramerized to furnish a new Zn(II)-1,6-methano[10]annulenecyanine which presents a strong red-shifted absorption band at 800 nm and high solubility in common organic solvents.<\/jats:p>","DOI":"10.3390\/molecules25092164","type":"journal-article","created":{"date-parts":[[2020,5,7]],"date-time":"2020-05-07T04:46:07Z","timestamp":1588826767000},"page":"2164","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of a Naphthalocyanine-Like Dye: The First Report on Zn(II)-1,6-methano[10]annulenecyanine"],"prefix":"10.3390","volume":"25","author":[{"given":"Nicholas Roberto da Silva","family":"Gobo","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade Federal de S\u00e3o Carlos, S\u00e3o Carlos CEP 13.565-905, S\u00e3o Paulo 01000-000, Brazil"},{"name":"ACCERT Chemistry and Biotechnology, S\u00e3o Carlos CEP 13.574-033, S\u00e3o Paulo 01000-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2215-0248","authenticated-orcid":false,"given":"Timothy John","family":"Brocksom","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade Federal de S\u00e3o Carlos, S\u00e3o Carlos CEP 13.565-905, S\u00e3o Paulo 01000-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9131-4800","authenticated-orcid":false,"given":"Kleber Thiago","family":"de Oliveira","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade Federal de S\u00e3o Carlos, S\u00e3o Carlos CEP 13.565-905, S\u00e3o Paulo 01000-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2020,5,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2738","DOI":"10.1039\/C9CS00059C","article-title":"Phthalocyanines and porphyrinoid analogues as hole- and electron-transporting materials for perovskite solar cells","volume":"48","author":"Urbani","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"4585","DOI":"10.1002\/ejoc.201400147","article-title":"Synthesis of a Fully Conjugated Phthalocyanine-Diketopyrrolopyrrole-Phthalocyanine Triad as Low Band Gap Donor in Small Molecule Bulk Heterojunction Solar Cells","volume":"2014","author":"Molina","year":"2014","journal-title":"Eur. J. Org. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"107939","DOI":"10.1016\/j.dyepig.2019.107939","article-title":"Fluorosubstituted lead phthalocyanines: Crystal structure, spectral and sensing properties","volume":"173","author":"Kuprikova","year":"2020","journal-title":"Dyes Pigments"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"18720","DOI":"10.1007\/s10854-019-02225-9","article-title":"Cobalt phthalocyanine polymer for optoelectronic and thermoelectric applications","volume":"30","author":"Aliabad","year":"2019","journal-title":"J. Mater. Sci. Mater. Electron."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"13554","DOI":"10.1021\/jp307825u","article-title":"New Columnar Zn-Phthalocyanine Designed for Electronic Applications","volume":"116","author":"Bechtold","year":"2012","journal-title":"J. Phys. Chem. B"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"9666","DOI":"10.1039\/C6NJ02073A","article-title":"Improved photodynamic activity of a dual phthalocyanine\u2013ALA photosensitiser","volume":"40","author":"Pavani","year":"2016","journal-title":"New J. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1002\/cptc.201900020","article-title":"Photoinactivation of Planktonic and Biofilm Forms of Escherichia coli through the Action of Cationic Zinc(II) Phthalocyanines","volume":"3","author":"Rocha","year":"2019","journal-title":"ChemPhotoChem"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1016\/j.jphotochem.2012.12.009","article-title":"Photophysical properties and photodynamic activity of a novel menthol\u2013zinc phthalocyanine conjugate incorporated in micelles","volume":"253","author":"Romero","year":"2013","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"110462","DOI":"10.1016\/j.msec.2019.110462","article-title":"Phthalocyanine-loaded nanostructured lipid carriers functionalized with folic acid for photodynamic therapy","volume":"108","author":"Sato","year":"2020","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.inoche.2018.11.004","article-title":"Design, synthesis and photobiological activity of novel ruthenium phthalocyanine complexes","volume":"99","author":"Negri","year":"2019","journal-title":"Inorg. Chem. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Revuelta-Maza, M.\u00c1., Mascaraque, M., Gonz\u00e1lez-Jim\u00e9nez, P., Gonz\u00e1lez-Camu\u00f1as, A., Nonell, S., Juarranz, \u00c1., de la Torre, G., and Torres, T. (2020). Assessing Amphiphilic ABAB Zn(II) Phthalocyanines with Enhanced Photosensitization Abilities in In Vitro Photodynamic Therapy Studies Against Cancer. Molecules, 25.","DOI":"10.3390\/molecules25010213"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4688","DOI":"10.1021\/acs.jmedchem.6b00054","article-title":"Phthalocyanine Labels for Near-Infrared Fluorescence Imaging of Solid Tumors","volume":"59","author":"Lobo","year":"2016","journal-title":"J. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1041","DOI":"10.1039\/C9CS00129H","article-title":"The unique features and promises of phthalocyanines as advanced photosensitisers for photodynamic therapy of cancer","volume":"49","author":"Lo","year":"2020","journal-title":"Chem. Soc. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"316","DOI":"10.1016\/j.dyepig.2013.05.012","article-title":"Synthesis of unsymmetrical phthalocyanine derivatives and their interaction with mammary MCF7 cells","volume":"99","author":"Manieri","year":"2013","journal-title":"Dyes Pigments"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1402","DOI":"10.1039\/C5OB02228B","article-title":"NIR bacteriochlorin chromophores accessed by Heck and Sonogashira cross-coupling reactions on a tetrabromobacteriochlorin derivative","volume":"14","author":"Ferreira","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Barona-Casta\u00f1o, J., Carmona-Vargas, C., Brocksom, T., and de Oliveira, K. (2016). Porphyrins as Catalysts in Scalable Organic Reactions. Molecules, 21.","DOI":"10.3390\/molecules21030310"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3602","DOI":"10.1038\/s41467-019-11542-w","article-title":"CO2 electrochemical catalytic reduction with a highly active cobalt phthalocyanine","volume":"10","author":"Wang","year":"2019","journal-title":"Nat. Commun."},{"key":"ref_18","first-page":"1199","article-title":"Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives","volume":"29","author":"Antonio","year":"2017","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1016\/j.dyepig.2017.12.065","article-title":"Multicomponent reactions mediated by NbCl 5 for the synthesis of phthalonitrile-quinoline dyads: Methodology, scope, mechanistic insights and applications in phthalocyanine synthesis","volume":"151","author":"Brocksom","year":"2018","journal-title":"Dyes Pigments"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Pekbelgin Karao\u011flu, H., and Kalkan Burat, A. (2020). \u03b1- and \u03b2-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties. Molecules, 25.","DOI":"10.3390\/molecules25020363"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Abid, S., Ben Hassine, S., Richy, N., Camerel, F., Jamoussi, B., Blanchard-Desce, M., Mongin, O., Paul, F., and Paul-Roth, C.O. (2020). Phthalocyanine-Cored Fluorophores with Fluorene-Containing Peripheral Two-Photon Antennae as Photosensitizers for Singlet Oxygen Generation. Molecules, 25.","DOI":"10.3390\/molecules25020239"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jphotochem.2017.02.025","article-title":"The impact of the extended \u03c0-conjugation in photophysical, photochemical and aggregation behavior of new phthalocyanine\u2013naphthalocyanine hybrids","volume":"340","author":"Ribeiro","year":"2017","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Gobo, N.R.S., Brocksom, T.J., Zukerman-Schpector, J., and De Oliveira, K.T. (2013). Synthesis of an octa-tert-butylphthalocyanine: A low-aggregating and photochemically stable photosensitizer. Eur. J. Org. Chem., 5028\u20135031.","DOI":"10.1002\/ejoc.201300415"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"42","DOI":"10.2174\/15701794113106660085","article-title":"Chlorins: Natural Sources, Synthetic Developments and Main Applications","volume":"11","author":"Oliveira","year":"2014","journal-title":"Curr. Org. Synth."},{"key":"ref_25","first-page":"310","article-title":"Basic Concepts and Applications of Porphyrins, Chlorins and Phthalocyanines as Photosensitizers in Photonic Therapies","volume":"7","author":"Gobo","year":"2015","journal-title":"Rev. Virtual Qu\u00edm."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1132","DOI":"10.2174\/1570179414666170403115907","article-title":"Soluble and Non-Aggregated Phthalocyanines: Synthesis, Mechanistic Aspects and Their Main Building Blocks","volume":"14","author":"Gobo","year":"2018","journal-title":"Curr. Org. Synth."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"98","DOI":"10.3390\/molecules17010098","article-title":"Like a bolt from the blue: Phthalocyanines in biomedical optics","volume":"17","author":"Sekkat","year":"2012","journal-title":"Molecules"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1142\/S1088424610001799","article-title":"The key role of peripheral substituents in the chemistry of phthalocyanines and their analogs","volume":"14","author":"Lukyanets","year":"2010","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2433","DOI":"10.1016\/j.tet.2012.01.004","article-title":"Synthesis of unsymmetrical phthalocyanines: A brief overview","volume":"68","author":"Wang","year":"2012","journal-title":"Tetrahedron"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2792","DOI":"10.1016\/j.ccr.2010.05.002","article-title":"Synthetic pathways to water-soluble phthalocyanines and close analogs","volume":"254","author":"Dumoulin","year":"2010","journal-title":"Coord. Chem. Rev."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1021\/cr9003049","article-title":"Low Symmetry Phthalocyanines and Their Analogues","volume":"111","author":"Mack","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1021\/jo061702v","article-title":"Aromaticity and Homoaromaticity in Methano[10]annulenes","volume":"72","author":"Caramori","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1002\/ange.19640760309","article-title":"Synthese eines Cyclodecapentaens","volume":"76","author":"Vogel","year":"1964","journal-title":"Angew. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"9343","DOI":"10.1021\/ja00073a082","article-title":"Effects of amphiphile topology on aggregation properties: Distinctive behavior of contrafacial amphiphiles","volume":"115","author":"Barrett","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","unstructured":"Vogel, E., Sch\u00e4fer-Ridder, M., and Wagner, A. (1978). Neue Cycloheptatrien-Verbindungen und Verfahren zur Herstellung von Cycloheptatrien-Verbindungen. (EP0011669A1)."},{"key":"ref_36","first-page":"1149","article-title":"A novel synthesis of substituted 1,6- methano[10]annulenes using a phase transfer catalyst","volume":"32B","author":"Sarmah","year":"1993","journal-title":"Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"8736","DOI":"10.1021\/jo030201w","article-title":"Novel Efficient Preparative Method for Phthalocyanines from Phthalimides and Phthalic Anhydride with HMDS","volume":"68","author":"Uchida","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"5976","DOI":"10.1002\/ejoc.201402776","article-title":"A Short-Step Synthesis of 1,6-Methano[10]annulene-3,4-dicarboximides and Their Benzene-, Naphthalene-, and Thiophene-Annulated Compounds","volume":"2014","author":"Oda","year":"2014","journal-title":"Eur. J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"789","DOI":"10.3987\/COM-11-12135","article-title":"Synthesis and Emission Properties of 1,6-Methano[10]annulene-3,4-dicarboximides","volume":"83","author":"Kuroda","year":"2011","journal-title":"Heterocycles"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"822","DOI":"10.1039\/B315319C","article-title":"Photophysical and photochemical studies of zinc(ii) phthalocyanine derivatives\u2014effects of substituents and solvents","volume":"28","author":"Ogunsipe","year":"2004","journal-title":"New J. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"7404","DOI":"10.1021\/ja00336a019","article-title":"A silicon phthalocyanine and a silicon naphthalocyanine: Synthesis, electrochemistry, and electrogenerated chemiluminescence","volume":"106","author":"Wheeler","year":"1984","journal-title":"J. Am. Chem. Soc."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/9\/2164\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T13:25:23Z","timestamp":1760361923000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/9\/2164"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,5,5]]},"references-count":41,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2020,5]]}},"alternative-id":["molecules25092164"],"URL":"https:\/\/doi.org\/10.3390\/molecules25092164","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2020,5,5]]}}}