Gold‐Catalyzed Bidirectional Access to Planar Heptacyclic Benzobispyrido[1, 2‐a]indoles and Benzobispyrrolo[1, 2‐a]Quinolines for Materials Science. Issue 20 (6th October 2022)

• Record Type: Journal Article
• Authors: Heckershoff, Robin; Eberle, Lukas; May, Garrett; Krämer, Petra; Rominger, Frank; Rudolph, Matthias; Hashmi, A. Stephen K.
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 20(2022)
• Page Start: 3559
• Page End: 3566
• Publication Date: 2022-10-06
• Subjects: Gold catalysis -- Materials science -- Nitrogen heterocycles -- Organic semiconductors -- Photophysics; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200708
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Our recently developed gold‐catalyzed synthesis of indolo[1, 2‐ a ]quinolines was successfully expanded towards bidirectional approaches, enabling access to two heptacyclic structural motifs. In the case of benzobispyrido[1, 2‐ a ]indoles, previously inaccessible modifications of the only known representative were made possible. In addition, the synthesis of a new class of nitrogen‐containing heptacycles – namely benzobispyrrolo[1, 2‐ a ]quinolines – was achieved by applying alkynylated benzodipyrrole derivatives as starting materials. All new compounds alongside with their corresponding precursors were fully characterized and their properties were investigated by X‐ray crystallography, photophysical measurements and computational methods. The study revealed important structure‐effect relationships between the solid‐state structures and the observed photophysical properties, e. g. aggregation‐induced emission and solid‐state fluorescence. Abstract :