Facile preparation and fluorescence properties of a soluble oligopyrrole derivative

Zhang, Shihu; Lv, Guowei; Wang, Guolong; Zhu, Kaiming; Yu, Demei; Shao, Jinyou; Wang, Yanzhou; Liu, Yuhang

doi:10.1016/j.jphotochem.2015.04.023

Cited by 6 publications

(2 citation statements)

References 45 publications

(49 reference statements)

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“…The successful preparation of such a quaterpyrrole prompted us to generalize this synthetic methodology, giving a straightforward access to substituted bipyrroles 3 bearing aromatic and unsaturated moieties at positions 5,5′ (Scheme ). The conjugated structure and the presence of the bipyrrolic moiety make these new molecules of interest in the design of metal ligands, − macrocyclic receptors, ,,− molecular electronics, light-emitting diodes, electrochromic devices, molecular wires, the preparation of conjugated low band gap polymers, − and polymer-based sensors. − …”

Section: Introductionmentioning

confidence: 99%

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

et al. 2017

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The preparation and characterization of a family of stable 2,2'-bipyrroles substituted at positions 5 and 5' with thienyl, phenyl, TMS-ethynyl, and vinyl groups is reported herein. The synthesis of these new bipyrroles comprises three steps: formation of the corresponding 5,5'-unsubstituted bipyrrole, bromination, and Stille or Suzuki coupling. The best results in the coupling are obtained using the Stille reaction under microwave irradiation. The new compounds have been fully characterized by UV-vis absorption, fluorescence, and IR spectroscopies and cyclic voltammetry. X-ray single-crystal analysis of four of the synthesized bipyrroles indicates a trans coplanar geometry of the pyrrole rings. Furthermore, the substituents at positions 5,5' remain coplanar to the central rings. This particular geometry extends the π-conjugation of the systems, which is in agreement with a red-shifting observed for the λ of the substituted molecules compared to the unsubstituted bipyrrole. All of these new compounds display a moderate fluorescence. In contrast with unsubstituted bipyrroles, these bipyrroles are endowed with a high chemical and thermal stability and solubility in organic solvents.

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Section: Introductionmentioning

confidence: 99%

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

et al. 2017

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“…Organic photoluminescent materials have attracted much attention in recent years due to their importance in organic light emitting diodes (OLEDs) [ 1 , 2 , 3 , 4 , 5 ] and chemosensors [ 6 , 7 ]. Recently, 2,2′-bipyrrole ( Figure 1 A), which is also known as a building block of natural red pigments, has been extensively studied because of its luminescent properties and applications in the development of artificial tetrapyrrole and oligopyrrole systems [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Che et al have demonstrated that a bipyrrole can be a good candidate for the development of luminescent materials of OLEDs [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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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.

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Unraveling electronic properties of an organometallic solute: Lippert-Mataga and quantum-chemical extensive study

Loukova

Vasiliev

Milov

et al. 2016

Journal of Photochemistry and Photobiology A: Chemistry

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Facile preparation and fluorescence properties of a soluble oligopyrrole derivative

Cited by 6 publications

References 45 publications

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

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

Unraveling electronic properties of an organometallic solute: Lippert-Mataga and quantum-chemical extensive study

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