57103-03-4Relevant articles and documents
Synthesis and photophysical properties of a new carbazole-based acidochromic molecular switch
Heydari, Zahra,Rashidi-Ranjbar, Parviz
, p. 8 - 13 (2019)
A reversible color–changing and fluorescence molecular switch was designed and synthesized based on carbazole fluorophores and amino group receptors. The crab shape molecule 1 is not soluble in most organic solvents and showslow solubility in acetic acid and DMSO (1 mg/ml in DMSO). The solution of 1 in DMSO performed as single on/off switch triggered by acidic protons. The colorless solution in basic and neutral conditions turned to yellow upon addition of a small amount of acid together with quench in fluorescence emission. The solid state of 1 has a dual-mode fluorescence switching property. The creamy white powder of 1has an emission λmax at 398 nm but when exposed to acidic vapors or suspended into acidic mediathe color of the powder changed to yellow and its emission λmax appeared at 516 nm. Monte-Carlo simulation has been performed to search the conformational space of the neutral and acidic forms. The frontier molecular orbitals of the most stable conformers has been calculated using DFT/B3LYP method using 6–31 g (d) basis set in attempt to explain the difference in electronic transition of 1 and its porotonated form.
A nitrophenyl-carbazole based push-pull linker as a building block for non-linear optical active coordination polymers: A structural and photophysical study
Fischer, Roland A.,Hauer, Jürgen,Mayer, David C.,P?thig, Alexander,Thyrhaug, Erling,Weish?upl, Sebastian J.
, (2020/12/07)
Non-linear optical effects (NLO) such as multi-photon absorption, second harmonic generation (SHG) etc. have a wide range of applications. Nevertheless, the performance of many NLO-active organic dyes is limited by their thermal stability and photobleaching. These problems can be overcome by integrating the dyes into coordination polymers or metal-organic frameworks. Here, we present a structural and photophysical study of dipropyl-9-(4-nitrophenyl)-carbazole-3,6-dicarboxylate, a new “push-pull” organic dye molecule designed as a chromophore linker for NLO-active coordination polymers. Structure determination of a single-crystal showed that it crystallizes in a monoclinic crystal system P 21/c. The solvated chromophore exhibits two aromatic absorption bands at 250 nm and 275 nm as well as broad long wavelength band at 350 nm, which we assign to an intramolecular charge transfer state. Photoluminescence measurements in solvents of different polarities revealed two main effects: In nonpolar solvents, the spectrum shows an emission band at 360 nm, whereas in solvents with a higher polarity, the emission maximum broadens and redshifts. Solid-state emission measurement of sample powder exhibits an emission band at 520 nm which is redshifted compared to the measurements in solution, due to excimer formation in the solid-state. The optical as well as solvation-related properties of the investigated pigment render it to be a versatile ligand in coordination polymers.
A convenient preparation of 9 H -carbazole-3,6-dicarbonitrile and 9 H -carbazole-3,6-dicarboxylic acid
Weseliński, ?ukasz J.,Luebke, Ryan,Eddaoudi, Mohamed
, p. 596 - 599 (2014/03/21)
A catalytic, high yielding and scalable procedure for the synthesis of 9H-carbazole-3,6-dicarbonitrile has been developed. Subsequent hydrolysis of the dinitrile in the presence of a catalytic copper species (i.e., CuI) yields 9H-carbazole-3,6-dicarboxylic acid. Both compounds are versatile and fine-tunable organic building blocks and therefore offer potential in material science, medicinal and supramolecular chemistry. Georg Thieme Verlag Stuttgart New York.
