Pyrrole and Its Derivatives

Schofield, K.

doi:10.1007/978-1-4899-5892-1_4

Cited by 2 publications

(1 citation statement)

References 380 publications

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“…In comparison to the unfunctionalized parent DTP, a small bathochromic shift is seen in the π → π* transitions (∼8−10 nm). This is consistent with similar shifts seen upon N -functionalization of pyrroles, , and is reasonable considering that while the N -substituents reside at a node in the DTP HOMO, they do contribute to the DTP LUMO (Figure ).…”

Section: Resultssupporting

confidence: 86%

A Simple and Efficient Route to N-Functionalized Dithieno[3,2-b:2‘,3‘-d]pyrroles: Fused-Ring Building Blocks for New Conjugated Polymeric Systems

2003

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A general synthetic route has been developed for the simple and efficient preparation of N-functionalized dithieno[3,2-b:2',3'-d]pyrroles. These synthetic methods utilize N-functionalized N-(3'-thienyl)-3-aminothiophenes produced from the Pd-catalyzed amination of 3-bromothiophene with primary amines, followed by a one-pot bromination/cyclization process. This combination allows the convenient preparation of a variety of N-functionalized dithieno[3,2-b:2',3'-d]pyrroles (where substituent = hexyl, octyl, decyl, tert-butyl, and p-hexylphenyl) in good yield (65-82%). Characterization of the structure and reactivity of this class of compounds is also described, including electrochemical and photophysical data for all compounds and X-ray structural data for the octyl-, tert-butyl-, and p-hexylphenyl-functionalized compounds.

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Section: Resultssupporting

confidence: 86%

A Simple and Efficient Route to N-Functionalized Dithieno[3,2-b:2‘,3‘-d]pyrroles: Fused-Ring Building Blocks for New Conjugated Polymeric Systems

2003

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Use of the Nascent Isocyclic Ring to Anchor Assembly of the Full Skeleton of Model Chlorophylls

Wang

Lindsey

2019

J. Org. Chem.

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The chlorophyll skeleton contains a chlorin macrocycle and an annulated fifth (or isocyclic) ring bearing 131-oxo and 132-carbomethoxy substituents. The isocyclic ring has traditionally been constructed by annulation of an intact tetrapyrrole macrocycle. Here, a complementary route employs reaction of a gem-dimethyl-substituted dihydrodipyrrin–carboxaldehyde (AD half) and a dipyrromethane bearing a 3-methoxy-1,3-dioxopropyl group (BC half). A McMurry-like reaction of a 2-(2-nitro-5-oxohexyl)pyrrole was employed to construct the second pyrrole ring in one of three BC halves, whereas the other two were prepared by known routes. An AD half and a BC half were joined by Knoevenagel condensation at room temperature, affording the AD,BC-substituted 2-methoxycarbonyl-2-propenone. The subsequent reaction of three AD, BC-propenones (mixture of Z,E-isomers) in CH3CN containing InCl3 and In(OTf)3 at 80 °C afforded the chlorophyll skeleton as the chloroindium(III) chelate; the reaction proceeds via Nazarov cyclization (to form the isocyclic ring), SEAr (to construct the macrocycle), and 2e–,2H+ oxidation (to give the aromatic chromophore). The absorption spectra of the complexes closely resemble that of chlorophyll a. The present work exploits the nascent isocyclic ring as an anchor for directed assembly of the AD and BC halves, forming both the chlorin macrocycle and the isocyclic ring in a single-flask transformation.

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Pyrrole and Its Derivatives

Cited by 2 publications

References 380 publications

A Simple and Efficient Route to N-Functionalized Dithieno[3,2-b:2‘,3‘-d]pyrroles: Fused-Ring Building Blocks for New Conjugated Polymeric Systems

A Simple and Efficient Route to N-Functionalized Dithieno[3,2-b:2‘,3‘-d]pyrroles: Fused-Ring Building Blocks for New Conjugated Polymeric Systems

Use of the Nascent Isocyclic Ring to Anchor Assembly of the Full Skeleton of Model Chlorophylls

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