Synthesis of new fluorescent building blocks via the microwave-assisted annulation reaction of 1,1,2-trimethyl-1H-benzo[e]indole with acrylic acid and its derivatives

3,3,3′,3′-Tetramethyl-2,2′-diphenyl-3H,3′H-5,5′-biindole

“…Thus, in a continuation of our work devoted to studying the fluorescence properties of various fused [12][13][14] and aryl coupled [15][16][17] indole derivatives, and in view of the importance of biheterocyclic compounds in current organic chemistry, the aim of the present work was the synthesis of 3,3,3′,3′-tetramethyl-2,2′-diphenyl-3H,3′H-5,5′-biindole as a novel fluorescent building block, through the Ullmann-type homocoupling reaction of 5-iodo-3,3-trimethyl-2-phenyl-3H-indole.…”

“…For instance, 4,4′-bipyridine (I) is commonly used in the synthesis of viologen compounds for optoelectronic applications [7], 6,6′-biquinoline (II) was used to prepare luminescent one-dimensional coordination polymers [8], 9H,9′H-3,3′-bicarbazole (III) was used for the synthesis of a cross-linkable hole-transporting polymer for organic light-emitting diodes (OLEDs) [9], 1H,1′H-6,6′-biindole (IV) provides a core for glycoprotein 41 targeting HIV-1 fusion inhibitors [10], and 2,2′,3,3′-hexamethyl-3H,3′H-5,5′-biindole (V) was used to prepare reversible photoisomerization possessing bis-spiropyran derivatives [11] (Figure 1). Thus, in a continuation of our work devoted to studying the fluorescence properties of various fused [12][13][14] and aryl coupled [15][16][17] indole derivatives, and in view of the importance of biheterocyclic compounds in current organic chemistry, the aim of the present work was the synthesis of 3,3,3 ,3 -tetramethyl-2,2 -diphenyl-3H,3 H-5,5 -biindole as a novel fluorescent building block, through the Ullmann-type homocoupling reaction of 5-iodo-3,3-trimethyl-2-phenyl-3H-indole.…”

New Bioactive Aromatic Heterocyclic Macromolecules with Monosaccharide Core

“…Haribhau S. Kumbhar synthesized 1, 1, 2-trimethyl-1H benzo[e]indoline based β-enaminone boron complexes exhibited the intense fluorescence (11). Rasa Steponavičiūtė et al reported the reaction of 1,1,2trimethyl-1H-benzo[e]indole with acrylic acid and its derivatives was employed for the preparation of novel fluorescent building blocks (12). Rasa Steponavičiūtė was able to alkylate 1,1,2-trimethyl-1Hbenzo[e]indole with bifunctional compounds, and investigated their chemical and optical properties (13).…”

10a,11,11-Trimethyl-10a,11-dihydro-8H-benzo[e]imidazo[1,2-a]indol-9(10H)-one

“…Furthermore, organic squaraine dyes based on the N-quaternized 1,1,2-trimethyl-1H-benzo[e]indolium salts have been used for the preparation of dye-sensitized solar cells [9]. It was recently shown by us that the microwave-assisted reaction of 1,1,2-trimethyl-1H-benzo[e]indole with acrylamide or acrylic acid gave functionalized benzo[e]indoline derivatives possessing intense fluorescence and significant Stokes shifts [10]. The aim of the present work is the synthesis of 10a,11,11-trimethyl-10a,11-dihydro-8H-benzo[e] imidazo[1,2-a]indol-9(10H)-one as a novel fluorescent building block, through the reaction of 1,1,2-trimethyl-1H-benzo[e]indole with 2-chloroacetamide.…”