We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3'4,4'-Tetraethyl-5,5'-divinyl-2,2'-bipyrrole Derivatives.
- Authors
Toru Okawara; Reo Kawano; Hiroya Morita; Finkelstein, Alan; Renjiro Toyofuku; Kanako Matsumoto; Kenji Takehara; Toshihiko Nagamura; Seiji Iwasa; Kumar, Sanjai
- Abstract
Photoluminescent divinylbipyrroles were synthesized from 3,3',4,4'-tetraetyl-2,2'- bipyrrole-5,5'-dicarboxaldehyde and activated methylene compounds via aldol condensation. For mechanistic clarity, molecular structures of Meldrum's 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's 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' 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.
- Subjects
PYRROLE derivatives; AROMATIC compound derivatives; CRYSTAL structure; ALDOL condensation; CONDENSATION reactions
- Publication
Molecules, 2017, Vol 22, Issue 11, p1816
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules22111816