{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T06:05:56Z","timestamp":1760853956985,"version":"build-2065373602"},"reference-count":47,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2017,10,26]],"date-time":"2017-10-26T00:00:00Z","timestamp":1508976000000},"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>Photoluminescent divinylbipyrroles were synthesized from 3,3\u2032,4,4\u2032-tetraetyl-2,2\u2032-bipyrrole-5,5\u2032-dicarboxaldehyde and activated methylene compounds via aldol condensation. For mechanistic clarity, molecular structures of Meldrum\u2019s acid- and 1,3-dimethylbarbituric acid-derived divinylbipyrroles were determined by single-crystal X-ray diffraction. Photoluminescent properties of the synthesized divinylbipyrroles in dichloromethane were found to be dependent on the presence of electron withdrawing groups at the vinylic terminal. The divinylbipyrroles derived from malononitrile, Meldrum\u2019s acid, and 1,3-dimethylbarbituric acid showed fluorescent peaks at 553, 576, and 602 nm respectively. Computational studies indicated that the alkyl substituents on the bipyrrole 3 and 3\u2032 positions increased energy level of the highest occupied molecular orbital (HOMO) compared to the unsubstituted derivatives and provided rationale for the bathochromic shift of the ultraviolet-visible (UV-Vis) spectra compared to the previously reported analogs.<\/jats:p>","DOI":"10.3390\/molecules22111816","type":"journal-article","created":{"date-parts":[[2017,10,26]],"date-time":"2017-10-26T06:48:14Z","timestamp":1509000494000},"page":"1816","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3\u2032,4,4\u2032-Tetraethyl-5,5\u2032-divinyl-2,2\u2032-bipyrrole Derivatives"],"prefix":"10.3390","volume":"22","author":[{"given":"Toru","family":"Okawara","sequence":"first","affiliation":[{"name":"Department of Creative Engineering, National Institute of Technology, Kitakyushu College, 5-20-1 Shi-i, Kokuraminami-ku, Kitakyushu 802-0985, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Reo","family":"Kawano","sequence":"additional","affiliation":[{"name":"Advanced School of Creative Engineering, National Institute of Technology, Kitakyushu College, 5-20-1 Shi-i, Kokuraminami-ku, Kitakyushu 802-0985, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroya","family":"Morita","sequence":"additional","affiliation":[{"name":"Advanced School of Creative Engineering, National Institute of Technology, Kitakyushu College, 5-20-1 Shi-i, Kokuraminami-ku, Kitakyushu 802-0985, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alan","family":"Finkelstein","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, Queens College, Queens, NY 11367, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Renjiro","family":"Toyofuku","sequence":"additional","affiliation":[{"name":"Department of Materials Science and Chemical Engineering, National Institute of Technology, Kitakyushu College, 5-20-1 Shi-i, Kokuraminami-ku, Kitakyushu 802-0985, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kanako","family":"Matsumoto","sequence":"additional","affiliation":[{"name":"Department of Materials Science and Chemical Engineering, National Institute of Technology, Kitakyushu College, 5-20-1 Shi-i, Kokuraminami-ku, Kitakyushu 802-0985, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kenji","family":"Takehara","sequence":"additional","affiliation":[{"name":"Department of Creative Engineering, National Institute of Technology, Kitakyushu College, 5-20-1 Shi-i, Kokuraminami-ku, Kitakyushu 802-0985, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Toshihiko","family":"Nagamura","sequence":"additional","affiliation":[{"name":"Department of Creative Engineering, National Institute of Technology, Kitakyushu College, 5-20-1 Shi-i, Kokuraminami-ku, Kitakyushu 802-0985, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Seiji","family":"Iwasa","sequence":"additional","affiliation":[{"name":"Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1799-9730","authenticated-orcid":false,"given":"Sanjai","family":"Kumar","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, Queens College, Queens, NY 11367, USA"},{"name":"Ph.D. Program in Chemistry and Ph.D. Program in Biochemistry, The Graduate Center of the City University of New York, New York, NY 10016, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2017,10,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1603253","DOI":"10.1002\/adma.201603253","article-title":"Recent Progress in Ionic Iridium(III) Complexes for Organic Electronic Devices","volume":"29","author":"Ma","year":"2017","journal-title":"Adv. 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