Solvatochromic properties of 3,6-di-tert-butyl-8H-indolo[3,2,1-de]acridin-8-one

Abstract

The spectral and photophysical properties of newly synthesized 3,6-di-tert-butyl-8H-indolo[3,2,1-de]acridin-8-one were studied.

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…The 8 H -indolo­[3,2,1- de ]­phenanthridin-8-one ( C49.1 , Chart ) and 8 H -indolo­[3,2,1- de ]­acridin-8-one ( C49.2 ) ring systems are of interest because of their structural relationship to alkaloids of the canthine family . Several syntheses of the parent C49.1 and its substituted derivatives were described, starting from the 1930s work of Plant and Tomlinson, , followed by contributions from Teitei, and Ghosh et al More recent work from Gómez-Lor and Echavarren, Bracher et al, Wiczk et al, and Xu, Yao, et al explored several synthetic approaches to C49.1 , employing different disconnections of the fused framework. Various aza-analogues of C49.1 , containing additional embedded nitrogens and, occasionally, additional fused rings, were reported by Berti et al, Shipchandler and Mitscher, Desarbre and Merour Markgraf et al, Poupon et al, Dang and Stadlbauer, Huet et al, , Sarragiotto et al,and Bracher et al. , Related lactam derivatives were synthesized by Ziegler et al ( C49.5 ), Wolfbeis ( C49.6 ), and Stadlbauer et al ( C49.7 ) .…”

Copper/β-diketone-catalysed N-arylation of carbazoles

“…29 Purication by ash chromatography (petroleum ether): a white solid (66 mg, 41%), mp ¼ 95-96 C; 1 H NMR (400 MHz, CDCl 3 ): d 8.14 (d, J ¼ 8.0 Hz, 2H), 7.84 (dd, J ¼ 8.0 Hz, J ¼ 1.2 Hz, 1H), 7.52-7.43 (m, 2H), 7.39 (t, J ¼ 8.0 Hz, 3H), 7.28 (t, J ¼ 8.0 Hz, 2H), 7.06 (d,J ¼ 8.0 Hz,2H), ppm; 13 C NMR (100 MHz, CDCl 3 ) : d 140.79, 136.69, 134.18, 131.09, 130.10, 128.77, 125.89, 123.79, 123.20, 120.31, 119.94, 109.98, ppm. 3,6-Di-tert-butyl-9-phenyl-9H-carbazole (2a). 30 Purication by ash chromatography (petroleum ether): a white solid (135 mg, 76%), mp ¼ 155 C; 1 H NMR (400 MHz, CDCl 3 ): d 8.23 (d,J ¼ 1.6 Hz,2H),4H),3H),7.42 (d,J ¼ 8.8 Hz,2H), 1.54 (s, 18H), ppm; 13 C NMR (100 MHz, CDCl 3 ): d 142. 84, 139.33, 138.26, 129.79, 127.01, 126.83, 123.63, 123.39, 116.26, 109.25, ppm. 3-Bromo-9-phenyl-9H-carbazole (2b).…”

Investigation of solvent effect on photophysical properties of some sulfonamides derivatives

“…Furthermore, high k nr values of compounds in polar solvents show that the main path of the excited state deactivation is internal conversion. 8 Herein, the increase in k nr in polar solvents can be associated with twisted intramolecular charge transfer (TICT) state. 26,27 Furthermore, hydrogen bond interactions, which cause intramolecular proton transfer from the solvent to molecule, may contribute to radiative transitions.…”

“…The physical properties and polarity parameters of all solvents used in the study are listed in Table 5. 8,24 The stock solution of all compounds was prepared in MeOH. A certain amount of fresh probe samples in different solutions was obtained from this stock solution by evaporating the solvent.…”

“…Furthermore, high k nr values of compounds in polar solvents show that the main path of the excited state deactivation is internal conversion. 8 Herein, the increase in k nr in polar solvents can be associated with twisted intramolecular charge transfer (TICT)…”