{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T14:00:50Z","timestamp":1790776850282,"version":"4.1.0"},"reference-count":77,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2023,3,25]],"date-time":"2023-03-25T00:00:00Z","timestamp":1679702400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004442","name":"National Science Centre, Poland","doi-asserted-by":"publisher","award":["UMO-2016\/22\/E\/ST5\/00472"],"award-info":[{"award-number":["UMO-2016\/22\/E\/ST5\/00472"]}],"id":[{"id":"10.13039\/501100004442","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This systematic study aimed at finding a correlation between molecular structure, solubility, self-assembly, and electronic properties of a homological series of N-alkylated naphthalene diimides (NDIs). NDIs are known for their n-type carrier mobility and, therefore, have potential in the field of organic electronics, photovoltaics, and sensors. For the purpose of this study, nine symmetrical N,N\u2032-dialkylated naphthalene diimides (NDIC3-NDIC11) were synthesized in the reaction of 1,4,5,8-naphthalenetetracarboxylic dianhydride with alkylamines ranging from propyl- to undecyl-. The NDIs were characterized by spectroscopic (NMR, UV-Vis, FTIR), microscopic, and thermal methods (TGA and DSC), and X-ray diffraction (XRD). Our experimental study, extensively referring to findings reported in the literature, indicated that the NDIs revealed specific trends in spectroscopic and thermal properties as well as solubility and crystal morphology. The solubility in good solvents (chloroform, toluene, dichlorobenzene) was found to be the highest for the NDIs substituted with the medium-length alkyl chains (NDIC5\u2013NDIC8). Systematic FTIR and XRD studies unraveled a distinct parity effect related to the packing of NDI molecules with odd or even numbers of methylene groups in the alkyl substituents. The NDIs with an even number of methylene groups in the alkyl substituents revealed low-symmetry (P1\u2212) triclinic packing, whereas those with an odd number of carbon atoms were generally monoclinic with P21\/c symmetry. The odd\u2013even parity effect also manifested itself in the overlapping of the NDIs\u2019 aromatic cores and, hence, the \u03c0-\u03c0 stacking distance (d\u03c0-\u03c0). The odd-numbered NDIs generally revealed slightly smaller d\u03c0-\u03c0 values then the even-numbered ones. Testing the NDIs using standardized field-effect transistors and unified procedures revealed that the n-type mobility in NDIC6, NDIC7, and NDIC8 was 10- to 30-fold higher than for the NDIs with shorter or longer alkyl substituents. Our experimental results indicate that N,N\u2032-alkylated NDIs reveal an optimum range of alkyl chain length in terms of solution processability and charge transport properties.<\/jats:p>","DOI":"10.3390\/molecules28072940","type":"journal-article","created":{"date-parts":[[2023,3,27]],"date-time":"2023-03-27T02:18:27Z","timestamp":1679883507000},"page":"2940","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides\u2014A Systematic Review of Molecules for Next-Generation Organic Electronics"],"prefix":"10.3390","volume":"28","author":[{"given":"Dorota","family":"Chlebosz","sequence":"first","affiliation":[{"name":"Department of Physical and Quantum Chemistry, Wroclaw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroclaw, Poland"},{"name":"The Leibniz Institute of Polymer Research, Hohe Strasse 6, D-01069 Dresden, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5856-8609","authenticated-orcid":false,"given":"Waldemar","family":"Goldeman","sequence":"additional","affiliation":[{"name":"Department of Medicinal and Organic Chemistry, Wroclaw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Krzysztof","family":"Janus","sequence":"additional","affiliation":[{"name":"Department of Physical and Quantum Chemistry, Wroclaw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroclaw, Poland"},{"name":"The Leibniz Institute of Polymer Research, Hohe Strasse 6, D-01069 Dresden, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Micha\u0142","family":"Szuster","sequence":"additional","affiliation":[{"name":"Department of Physical and Quantum Chemistry, Wroclaw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3345-4298","authenticated-orcid":false,"given":"Adam","family":"Kiersnowski","sequence":"additional","affiliation":[{"name":"Department of Physical and Quantum Chemistry, Wroclaw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroclaw, Poland"},{"name":"The Leibniz Institute of Polymer Research, Hohe Strasse 6, D-01069 Dresden, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"11218","DOI":"10.1039\/D0TA01160F","article-title":"Naphthalene diimide as a two-electron anolyte for aqueous and neutral pH redox flow batteries","volume":"8","author":"Medabalmi","year":"2020","journal-title":"J. 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