{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,25]],"date-time":"2025-10-25T12:29:25Z","timestamp":1761395365464,"version":"build-2065373602"},"reference-count":78,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2018,11,18]],"date-time":"2018-11-18T00:00:00Z","timestamp":1542499200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BD\/87786\/2012","UID\/QUI\/0686\/2016","PTDC\/CTM\/105597\/2008","UID\/QUI\/50006\/2013","POCI-01-0145-FEDER \u2013 007265"],"award-info":[{"award-number":["SFRH\/BD\/87786\/2012","UID\/QUI\/0686\/2016","PTDC\/CTM\/105597\/2008","UID\/QUI\/50006\/2013","POCI-01-0145-FEDER \u2013 007265"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC","award":["Project N\u00ba 022161"],"award-info":[{"award-number":["Project N\u00ba 022161"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of \u03c0-conjugated molecules, based on pyridazine and thiophene heterocycles 3a\u2013e, were synthesized using commercially, or readily available, coupling components, through a palladium catalyzed Suzuki-Miyaura cross-coupling reaction. The electron-deficient pyridazine heterocycle was functionalized by a thiophene electron-rich heterocycle at position six, and different (hetero)aromatic moieties (phenyl, thienyl, furanyl) were functionalized with electron acceptor groups at position three. Density Functional Theory (DFT) calculations were carried out to obtain information on the conformation, electronic structure, electron distribution, dipolar moment, and molecular nonlinear response of the synthesized push-pull pyridazine derivatives. Hyper-Rayleigh scattering in 1,4-dioxane solutions, using a fundamental wavelength of 1064 nm, was used to evaluate their second-order nonlinear optical properties. The thienylpyridazine functionalized with the cyano-phenyl moiety exhibited the largest first hyperpolarizability (\u03b2 = 175 \u00d7 10\u221230 esu, using the T convention) indicating its potential as a second harmonic generation (SHG) chromophore.<\/jats:p>","DOI":"10.3390\/molecules23113014","type":"journal-article","created":{"date-parts":[[2018,11,21]],"date-time":"2018-11-21T11:23:27Z","timestamp":1542799407000},"page":"3014","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis of Pyridazine Derivatives by Suzuki-Miyaura Cross-Coupling Reaction and Evaluation of Their Optical and Electronic Properties through Experimental and Theoretical Studies"],"prefix":"10.3390","volume":"23","author":[{"given":"Sara S. M.","family":"Fernandes","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5887-2966","authenticated-orcid":false,"given":"Jo\u00e3o","family":"Aires-de-Sousa","sequence":"additional","affiliation":[{"name":"LAQV and Departamento de Qu\u00edmica, Faculdade de Ci\u00eancias e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7968-5038","authenticated-orcid":false,"given":"Michael","family":"Belsley","sequence":"additional","affiliation":[{"name":"Centro de F\u00edsica, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7996-1626","authenticated-orcid":false,"given":"M. Manuela M.","family":"Raposo","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2018,11,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2249","DOI":"10.1021\/acs.chemrev.7b00443","article-title":"Pd metal catalysts for cross-couplings and related reactions in the 21st century: A critical review","volume":"118","author":"Biffis","year":"2018","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"602","DOI":"10.1002\/adsc.201700810","article-title":"Recent advances in palladium-catalyzed cross-coupling reactions at ppm to ppb molar catalyst loadings","volume":"360","author":"Roy","year":"2018","journal-title":"Adv. Synth. 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