{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T02:44:27Z","timestamp":1790217867231,"version":"4.1.0"},"reference-count":37,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2019,2,28]],"date-time":"2019-02-28T00:00:00Z","timestamp":1551312000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this work, two oligophenyleneimines type pentamers with terminal aldehydes, designated as DAFCHO (4,4\u2032-((((((2,5-bis(octyloxy)-1,4-phenylene)bis(methanylylidene))bis(azanyl ylidene))bis(9H-fluorene-7,2-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,5-bis(octyloxy) benzaldehyde)) and FDACHO (4,4\u2032-((((((2,5-bis(octyloxy)-1,4-phenylene)bis(methanylylidene))bis (azanylylidene))bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(2,5-bis(octyloxy) benzaldehyde)) were synthesized by mechanochemistry method using 2,5-bis(octyloxy) terephtal aldehyde and 2,7-diaminofluorene or 1,4-phenylenediamine. All compounds were spectroscopically characterized using 1H and 13C-NMR, FT-IR and mass spectrometry MALDITOF. The optical properties of the compounds were analyzed by UV-vis spectroscopy using different solvents. We observed that DAFCHO and FDACHO exhibit interesting photochromic properties when they are dissolved in chloroform and exposed to sunlight for 3, 5 and 10 min. The value of the energy band gap was calculated from the absorption spectra without irradiation Egap(optical). It was 2.50 eV for DAFCHO in chloroform solution, and it decreased to 2.34 eV when it is in films. For FDACHO, it was 2.41 eV in solution and 2.27 eV in film. HOMO (Highest Occupied Molecular Orbital), LUMO (Lowest Unoccupied Molecular Orbital) and Egap(electrochemical) values were obtained by electrochemical studies. The results indicate that the compounds can be considered as organic semiconductors since their values are 2.35 eV for DAFCHO and 2.06 eV for FDACHO. The structural and electronic properties of the compounds were corroborated with a DFT (Density Functional Theory) study.<\/jats:p>","DOI":"10.3390\/molecules24050849","type":"journal-article","created":{"date-parts":[[2019,3,1]],"date-time":"2019-03-01T03:33:00Z","timestamp":1551411180000},"page":"849","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Mechanosynthesis of Photochromic Oligophenyleneimines: Optical, Electrochemical and Theoretical Studies"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8126-3811","authenticated-orcid":false,"given":"Miguel Angel","family":"Amado-Brise\u00f1o","sequence":"first","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8696-1288","authenticated-orcid":false,"given":"Luis \u00c1ngel","family":"Z\u00e1rate-Hern\u00e1ndez","sequence":"additional","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6716-7049","authenticated-orcid":false,"given":"Karina","family":"Alem\u00e1n-Ayala","sequence":"additional","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oscar","family":"Core\u00f1o Alonso","sequence":"additional","affiliation":[{"name":"Dpto. 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Civil, Universidad de Guanajuato, Ju\u00e1rez 77, Guanajuato CP 36000, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1218-3719","authenticated-orcid":false,"given":"Juli\u00e1n","family":"Cruz-Borbolla","sequence":"additional","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Manuel","family":"V\u00e1squez-P\u00e9rez","sequence":"additional","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"V\u00edctor Esteban","family":"Reyes-Cruz","sequence":"additional","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3453-1227","authenticated-orcid":false,"given":"Mar\u00eda Aurora","family":"Veloz-Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Esteban","family":"Rueda-Soriano","sequence":"additional","affiliation":[{"name":"\u00c1rea Acad\u00e9mica de Ciencias de la Tierra y Materiales, \u00c1rea Acad\u00e9mica de Computaci\u00f3n y Electr\u00f3nica, \u00c1rea Acad\u00e9mica de Qu\u00edmica, Universidad Aut\u00f3noma del Estado de Hidalgo, Ciudad Universitaria, Pachuca CP 42184, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7302-4044","authenticated-orcid":false,"given":"Thangarasu","family":"Pandiyan","sequence":"additional","affiliation":[{"name":"Facultad de Qu\u00edmica, UNAM, Cd. 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