{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,28]],"date-time":"2026-01-28T06:24:27Z","timestamp":1769581467017,"version":"3.49.0"},"reference-count":23,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2012,9,7]],"date-time":"2012-09-07T00:00:00Z","timestamp":1346976000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Novel sandwich-type phthalocyanines containing a rare earth metal core (Pr, Nd, Eu\u2013Lu) and macrocycles peripherally substituted by pentadecylphenoxy groups were synthesized using a cardanol-based phthalonitrile precursor and the respective lanthanide acetate. Additionally, the metal free-base analog compound was studied for comparison. The purified reaction products were all found to be thick and viscous substances at room temperature, showing liquid crystalline behavior with a distinct increase in fluidity at ca. 40 \u00b0C. The complexes are readily soluble in chloroalkyl solvents and dissolve fairly well in DMF with some tendency to form aggregates. Besides they are strongly hydrophobic and reveal a peculiar affinity for lipophilic media. The compounds have been characterized by UV-Vis (absorption and emission), FTIR, MS and DSC methods. Photochemical activity in the liquid phase (dimethylformamide, dichloromethane, mineral oil) and the degree of photodegradation demonstrated under constant UV-irradiation (\u03bb = 352 nm) have been analyzed and discussed in terms of photostability.<\/jats:p>","DOI":"10.3390\/molecules170910738","type":"journal-article","created":{"date-parts":[[2012,9,7]],"date-time":"2012-09-07T11:21:14Z","timestamp":1347016874000},"page":"10738-10753","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Novel Lipophilic Lanthanide Bis-Phthalocyanines Functionalized by Pentadecylphenoxy Groups: Synthesis, Characterization and UV-Photostability"],"prefix":"10.3390","volume":"17","author":[{"given":"Rudolf","family":"S\u0142ota","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gabriela","family":"Dyrda","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria","family":"Hofer","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Giuseppe","family":"Mele","sequence":"additional","affiliation":[{"name":"Department of Engineering for Innovation, University of Salento, Via Arnesano, 73100 Lecce, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ermelinda","family":"Bloise","sequence":"additional","affiliation":[{"name":"Department of Engineering for Innovation, University of Salento, Via Arnesano, 73100 Lecce, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Roberta del","family":"Sole","sequence":"additional","affiliation":[{"name":"Department of Engineering for Innovation, University of Salento, Via Arnesano, 73100 Lecce, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2012,9,7]]},"reference":[{"key":"ref_1","first-page":"335","article-title":"Synthesis of erbium phthalocyanine","volume":"9","author":"Plyushev","year":"1964","journal-title":"Zh. Neorg. Khim. (Russ. J. Inorg. Chem.)"},{"key":"ref_2","first-page":"1951","article-title":"Formation of unusual rare earth metal phthalocyanines","volume":"10","author":"Kirin","year":"1965","journal-title":"Zh. Neorg. Khim. (Russ. J. Inorg. Chem.)"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Simon, J., and Andr\u00e9, J.J. (1985). Molecular Semiconductors, Springer-Verlag.","DOI":"10.1007\/978-3-642-70012-5"},{"key":"ref_4","unstructured":"Leznoff, C.C., and Lever, A.B.P. (1989\u20131996). Phthalocyanines Properties and Applications, VCH. [1st]."},{"key":"ref_5","unstructured":"Kadish, K., Smith, K.M., and Guilard, R. (2006). The Porphyrin Handbook, Academic Press Inc.. [1st]."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"875","DOI":"10.1070\/RC2008v077n10ABEH003879","article-title":"Synthetic approaches to lanthanide complexes with tetrapyrrole type ligands","volume":"77","author":"Pushkarev","year":"2008","journal-title":"Russ. Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5743","DOI":"10.1021\/ic0260217","article-title":"UV photostability of metal phthalocyanines in organic solvents","volume":"42","author":"Dyrda","year":"2003","journal-title":"Inorg. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1007\/s10562-008-9609-z","article-title":"Sulfur dioxide oxidation catalyzed by photosensitized ytterbium diphthalocyanine","volume":"126","author":"Dyrda","year":"2008","journal-title":"Catal. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"124","DOI":"10.1016\/0009-2614(85)85490-7","article-title":"Synthesis and physico-chemical studies of neutral and chemically oxidized forms of bis (octaalkyloxyphthalocyaninato) lutetium","volume":"122","author":"Piechocki","year":"1985","journal-title":"Chem. Phys. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"8105","DOI":"10.1021\/j100361a026","article-title":"Electrical and magnetic properties of liquid crystalline molecular materials: Lithium and lutetium phthalocyanine derivatives","volume":"93","author":"Belarbi","year":"1989","journal-title":"J. Phys. Chem."},{"key":"ref_11","first-page":"223","article-title":"Phthalocyanine based liquid crystals: Towards submicronic devices","volume":"Volume 2","author":"Leznoff","year":"1993","journal-title":"Phthalocyanines Properties and Applications"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1039\/JM9940400533","article-title":"Chromic materials. Part 1. Liquid-crystalline behaviour and electrochromism in bis (octakis-n-alkylphthalocyaninato) lutetium (III) complexes","volume":"4","author":"Komatsu","year":"1994","journal-title":"J. Mater. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"537","DOI":"10.1039\/JM9940400537","article-title":"Discotic liquid crystals of transition-metal complexes. Part 18. Discotic liquid crystalline behaviour in phthalocyanine compounds substituted by steric hindrance groups at the core","volume":"4","author":"Komatsu","year":"1994","journal-title":"J. Mater. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1667","DOI":"10.1021\/ic051754n","article-title":"Synthesis, Structure, And spectroscopic and magnetic properties of mesomorphic octakis (hexylthio)-substituted phthalocyanine rare-earth metal sandwich complexes","volume":"45","author":"Basova","year":"2006","journal-title":"Inorg. Chem."},{"key":"ref_15","first-page":"1","article-title":"Liquid crystals of phthalocyanines, Porphyrins and related compounds","volume":"Volume 12","author":"Kadish","year":"2011","journal-title":"Handbook of Porphyrin Science"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2426","DOI":"10.1007\/s11172-007-0385-5","article-title":"Synthesis and spectral characteristics of cyclohexylmethoxy-substituted phthalocyanines of rare-earth elements","volume":"56","author":"Kalashnikova","year":"2007","journal-title":"Russ. Chem."},{"key":"ref_17","unstructured":"Tyman, J.H.P. (1996). Synthetic and Natural Phenols, Elsevier."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"243","DOI":"10.2174\/157019308785161611","article-title":"Fine chemicals and new hybrid materials from cardanol","volume":"5","author":"Mele","year":"2008","journal-title":"Mini-Rev. Org. Chem."},{"key":"ref_19","first-page":"799","article-title":"Synthesis of fullerene-cardanol derivatives","volume":"5","author":"Attanasi","year":"2004","journal-title":"Synlett"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1142\/S1088424603000082","article-title":"Novel phthalocyanines containing cardanol derivatives","volume":"7","author":"Attanasi","year":"2003","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"6581","DOI":"10.1021\/jp070529j","article-title":"Photocatalytic degradation of 4-nitrophenol in aqueous suspension by using polycrystalline TiO2 impregnated with lanthanide double-decker phthalocyanine complexes","volume":"111","author":"Mele","year":"2007","journal-title":"J. Phys. Chem.C"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1007\/s00775-010-0715-1","article-title":"Metalloporphyrin intercalation in liposome membranes: ESR study","volume":"16","author":"Man","year":"2011","journal-title":"J. Biol. Inorg. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1142\/S1088424606000065","article-title":"Effect of air absorbed oxygen and moisture on the chemical stability of photoexcited phthalocyanines in dimethylformamide","volume":"10","author":"Dyrda","year":"2006","journal-title":"J. Porphyr. Phthalocyanines"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/9\/10738\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:52:13Z","timestamp":1760219533000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/9\/10738"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,9,7]]},"references-count":23,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2012,9]]}},"alternative-id":["molecules170910738"],"URL":"https:\/\/doi.org\/10.3390\/molecules170910738","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,9,7]]}}}