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Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3',4,4'-Tetraethyl-5,5'-divinyl-2,2'-bipyrrole Derivatives.

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.

SUBMITTER: Okawara T 

PROVIDER: S-EPMC6150395 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Synthesis, Crystal Structure, and Photoluminescent Properties of 3,3',4,4'-Tetraethyl-5,5'-divinyl-2,2'-bipyrrole Derivatives.

Okawara Toru T   Kawano Reo R   Morita Hiroya H   Finkelstein Alan A   Toyofuku Renjiro R   Matsumoto Kanako K   Takehara Kenji K   Nagamura Toshihiko T   Iwasa Seiji S   Kumar Sanjai S  

Molecules (Basel, Switzerland) 20171026 11

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 g  ...[more]

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