{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T15:34:04Z","timestamp":1791041644231,"version":"4.1.0"},"reference-count":41,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2019,11,10]],"date-time":"2019-11-10T00:00:00Z","timestamp":1573344000000},"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>Isoquinoline derivatives have attracted great interest for their wide biological and fluorescent properties. In the current study, we focused on the synthesis of a series of novel isoquinoline derivatives substituted at position 3 of the heteroaromatic ring. Compounds were obtained in a Goldberg\u2013Ullmann-type coupling reaction with appropriate amides in the presence of copper(I) iodide, N,N-dimethylethylenediamine (DMEDA), and potassium carbonate. The structures of novel isoquinolines were confirmed by IR, NMR, and elemental analysis, as well as X-ray crystallography. In the course of our research work, the visible fluorescence of this class of compounds was observed. The above findings prompted us to investigate the optical properties of the selected compounds.<\/jats:p>","DOI":"10.3390\/molecules24224070","type":"journal-article","created":{"date-parts":[[2019,11,12]],"date-time":"2019-11-12T04:07:07Z","timestamp":1573531627000},"page":"4070","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Synthesis and Fluorescent Properties of Novel Isoquinoline Derivatives"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5234-1198","authenticated-orcid":false,"given":"\u0141ukasz","family":"Balewski","sequence":"first","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, 80-416 Gda\u0144sk, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Franciszek","family":"S\u0105czewski","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, 80-416 Gda\u0144sk, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria","family":"Gdaniec","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Adam Mickiewicz University, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anita","family":"Kornicka","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, 80-416 Gda\u0144sk, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karolina","family":"Cicha","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, 80-416 Gda\u0144sk, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aleksandra","family":"Jali\u0144ska","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda\u0144sk, 80-416 Gda\u0144sk, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,11,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"745","DOI":"10.1021\/np50047a001","article-title":"Simple isoquinoline alkaloids","volume":"49","author":"Menachery","year":"1986","journal-title":"J. Nat. Prod."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3613","DOI":"10.1021\/ol061525k","article-title":"Chaetoindicins A-C, three isoquinoline alkaloids from the fungus Chaetomium indicum","volume":"8","author":"Li","year":"2006","journal-title":"Org. Lett."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1140","DOI":"10.1021\/jm00257a003","article-title":"Pyrrolo [4,3,2-de]isoquinolines with central nervous system and antihypertensive activities","volume":"17","author":"Demerson","year":"1974","journal-title":"J. Med. Chem."},{"key":"ref_4","first-page":"200","article-title":"Molecular docking, design, synthesis, in vitro antioxidant and anti-inflammatory evaluations of new isoquinoline derivatives","volume":"7","author":"Alagumuthu","year":"2015","journal-title":"Int. J Pharm. Pharm. Sci."},{"key":"ref_5","first-page":"339","article-title":"Analgesic, anti-inflammatory and antipyretic evaluations of new isoquinoline derivatives","volume":"8","author":"Manikandan","year":"2016","journal-title":"J. Pharm. Sci."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3221","DOI":"10.1016\/j.bmc.2013.03.042","article-title":"Novel isoquinoline derivatives as antimicrobial agents","volume":"21","author":"Moreno","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"988","DOI":"10.3390\/molecules15020988","article-title":"Synthesis, cytotoxic and antimalarial activities of benzoyl thiosemicarbazone analogs of isoquinoline and related compounds","volume":"15","author":"Pingaew","year":"2010","journal-title":"Molecules"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1016\/j.ejmech.2012.11.042","article-title":"Antidepressant and antipsychotic activity of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole targeting serotonin 5-HT1A\/5-HT2A\/5-HT7 and dopamine D2\/D3 receptors","volume":"60","author":"Zajdel","year":"2013","journal-title":"Eur. J. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"895","DOI":"10.5560\/znb.2013-3101","article-title":"A novel route to isoquinoline[2,1-g][1,6]naphthyridine, pyrazolo[5,1-a] isoquinoline and pyridazino[4\u2019,5\u00b4:3,4]pyrazolo[5,1-a]isoquinoline derivatives with evaluation of antitumor activities","volume":"68","author":"Hassaneen","year":"2013","journal-title":"Z. Naturforsch."},{"key":"ref_10","first-page":"71","article-title":"Design, synthesis and cytotoxicity evaluation of new 2-aryl-5, 6-dihydropyrrolo[2,1-a]isoquinoline derivatives as topoisomerase inhibitors","volume":"13","author":"Kakhki","year":"2014","journal-title":"Iran J. Pharm. Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"923","DOI":"10.1002\/(SICI)1097-0215(19990611)81:6<923::AID-IJC14>3.0.CO;2-D","article-title":"Berberine-induced apoptosis of human leukemia HL-60 cells is associated with down-regulation of nucleophosmin\/B23 and telomerase activity","volume":"81","author":"Wu","year":"1999","journal-title":"Int. J. Cancer"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3688","DOI":"10.1021\/jm000029d","article-title":"Synthesis of new indeno[1,2-c]isoquinolines: cytotoxic non-camptothecin topoisomerase I inhibitors","volume":"43","author":"Cushman","year":"2000","journal-title":"J. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"109","DOI":"10.3998\/ark.5550190.0013.511","article-title":"Novel fluorescent isoquinoline derivatives obtained via Buchwald-Hartwig coupling of isoquinolin-3-amines","volume":"5","author":"Balog","year":"2012","journal-title":"ARKIVOC"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5264","DOI":"10.1016\/j.tetlet.2011.07.143","article-title":"New fluorescent isoquinoline derivatives","volume":"52","author":"Balog","year":"2011","journal-title":"Tetrahedron Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"4293","DOI":"10.1016\/j.tet.2009.03.063","article-title":"Aminoisoquinolines as colorimetric Hg2+ sensors: The importance of molecular structure and sacrificial base","volume":"65","author":"Wan","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Evans, D.A., Smith, G.F., and Wahid, M.A. (1967). The tautomerism of 3-hydroxyisoquinolines. J. Chem. Soc. (B), 590\u2013595.","DOI":"10.1039\/j29670000590"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1016\/0301-0104(76)87028-0","article-title":"Temperature dependence of radiationless processes. Isoquinoline in solution","volume":"16","author":"Huber","year":"1976","journal-title":"Chem. Phys."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2243","DOI":"10.1021\/j100561a022","article-title":"Luminescence studies of proton transfer in the excited electronic states of hydrogen bonded quinoline and isoquinoline","volume":"80","author":"Moomaw","year":"1976","journal-title":"J. Phys. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1016\/0009-2614(78)85041-6","article-title":"High pressure studies of isoquinoline luminescence in polymeric media","volume":"59","author":"Rollinson","year":"1978","journal-title":"Chem. Phys. Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"507","DOI":"10.1016\/0009-2614(79)80751-4","article-title":"Temperature effects on S1-S0\/S1-T1 branching ratio in radiationless transitions of N-heterocyclic compounds","volume":"62","author":"Lai","year":"1979","journal-title":"Chem. Phys. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1053","DOI":"10.1021\/jp973173s","article-title":"Conjugated dual hydrogen-bond mediating proton-transfer reaction in 3-hydroxyisoquinoline","volume":"102","author":"Wei","year":"1998","journal-title":"J. Phys. Chem. B"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1016\/j.saa.2004.05.030","article-title":"DFT studies and vibrational spectra of isoquinoline and 8-hydroxyquinoline","volume":"61","author":"Krishnakumar","year":"2005","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/j.cplett.2007.09.046","article-title":"Effect of ion pairing on the fluorescence of berberine, a natural isoquinoline alkaloid","volume":"447","author":"Megyesi","year":"2007","journal-title":"Chem. Phys. Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1002\/jhet.310","article-title":"Solvent-dependent fluorescence emission in heterocyclic compounds having isoquinoline backbone","volume":"47","author":"Singh","year":"2010","journal-title":"J. Heterocyclic Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"7272","DOI":"10.1021\/jp210516t","article-title":"Steady state and time-resolved fluorescence study of isoquinoline: Reinvestigation of excited state proton transfer","volume":"116","author":"Joshi","year":"2012","journal-title":"J. Phys. Chem. A"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2620","DOI":"10.1021\/cr900263j","article-title":"New strategies for fluorescent probe design in medical diagnostic imaging","volume":"110","author":"Kobayashi","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3232","DOI":"10.1016\/j.tetlet.2010.04.064","article-title":"Mild, convenient and versatile Cu-mediated synthesis of N-aryl-2-imidazolidinones","volume":"51","author":"Stabile","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"7421","DOI":"10.1021\/ja0260465","article-title":"A general and efficient copper catalyst for the amidation of aryl halides","volume":"124","author":"Klapars","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1515\/hc-2013-0125","article-title":"Synthesis of N-(2-pyridyl)imidazolidin-2-ones and 1-(2-pyridyl)-2,3,7,8-tetrahydro-1H-imidazo[2,1-b][1,3,5]triazepin-5(6H)-ones with potential biological activities","volume":"19","author":"Balewski","year":"2013","journal-title":"Heterocycl. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2649","DOI":"10.1002\/anie.201410290","article-title":"\u03b2--Strand Mimetic Foldamers Rigidified through Dipolar Repulsion","volume":"54","author":"German","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6521","DOI":"10.1039\/C6CC01496H","article-title":"Acid-mediated topological control in a functionalized foldamer","volume":"52","author":"Knipe","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3902","DOI":"10.1021\/acs.orglett.8b01483","article-title":"Palladium-catalyzed site-selective amidation of dichloroazines","volume":"20","author":"Young","year":"2018","journal-title":"Org. Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"17026","DOI":"10.3390\/molecules191017026","article-title":"Structural diversity of copper(II) complexes with N-(2-pyridyl)imidazolidin-2-ones(thiones) and their in vitro antitumor activity","volume":"19","author":"Balewski","year":"2014","journal-title":"Molecules"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2271","DOI":"10.1021\/jp963263h","article-title":"Fluorescence spectral study of 9-acridinecarboxylic acid and its methyl ester. Understanding the unusual fluorescence behavior of 9-anthroic acid","volume":"101","author":"Dey","year":"1997","journal-title":"J. Phys. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.saa.2007.03.024","article-title":"Fluorescence quenching of versatile fluorescent probes based on strongly electron-donating distyrylbenzenes responsive to aromatic chlorinated and nitro compounds, boronic acid and Ca2+","volume":"69","author":"Motoyoshiya","year":"2008","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1002\/bio.1205","article-title":"Fluorescence quenching studies of nitrated polycyclic aromatic hydrocarbons","volume":"26","author":"Miller","year":"2011","journal-title":"Luminescence"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1111\/j.1751-1097.1967.tb08790.x","article-title":"Quantitative spectrofluorimetry - the fluorescence quantum yield of quinine sulfate","volume":"6","author":"Eastman","year":"1967","journal-title":"Photochem. Photobiol."},{"key":"ref_38","unstructured":"Rigaku Oxford Diffraction (2015). CrysAlisPro Software system, version 1.171.38.46, Rigaku Corporation."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"ref_40","first-page":"3","article-title":"SHELXT - Integrated Space-Group and Crystal-Structure Determination","volume":"A71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_41","first-page":"3","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/22\/4070\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:33:24Z","timestamp":1760189604000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/22\/4070"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11,10]]},"references-count":41,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2019,11]]}},"alternative-id":["molecules24224070"],"URL":"https:\/\/doi.org\/10.3390\/molecules24224070","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,11,10]]}}}