Improved, Highly Efficient, and Green Synthesis of Bromofluorenones and Nitrofluorenones in Water

Zhang, Xin; Han, Jiande; Li, Pengfei; Ji, Xuan; Zhang, Zhao

doi:10.1080/00397910902838904

Cited by 28 publications

(15 citation statements)

References 10 publications

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“…Examples of synthetic procedures for selected key compounds are given in the following text. Synthetic details for other compounds can be found in the Supporting Information …”

Section: Methodsmentioning

confidence: 99%

“…Synthetic details for other compounds can be found in the Supporting Information. [26,[52][53][54][55][56][57] Generalp rocedure A-Steglich-typeesterification:Synthesis of P2 5-Diethylamino-2-iodobenzyl alcohol (10.0 g, 32.8 mmol, 1.0 equiv) was dissolved in CH 2 Cl 2 (100 mL). EDC-HCl (10.0 g, 52.3 mmol, 1.6 equiv), DIPEA (5.07 g, 39.3 mmol, 1.2 equiv), DMAP (0.4 g, 3.3 mmol, 0.1 equiv), and N-(tert-butoxycarbonyl)-l-glutamic acid 1tert-butyl ester (15.0 g, 49.5 mmol, 1.5 equiv) were added to the solution.…”

Section: Organic Synthesismentioning

confidence: 99%

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A New Photocage Derived from Fluorene

Reinfelds

Cosel

Falahati

et al. 2018

Chemistry A European J

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Photolabile protecting groups (PPGs or photocages) are increasingly subject to molecular design to meet requirements such as absorbance in the visible spectral range, high molar absorption coefficients, and high quantum yields of leaving group release. Improvements in these properties for the promising 3-diethylaminobenzyl (DEAMb) photocage, the photoactivity of which is based on the Zimmerman meta effect, are reported. Expansion of the aromatic system with a second aromatic ring resulted in improved spectral properties. A systematic trend relating the electronic (π-donor or acceptor) properties of the new aryl substituent and its position in the DEAMb ring to changes in the spectral properties could be observed. Conclusions from the experimental results were supported by computations obtained by using time-dependent DFT. A second generation of DEAMb-based photocages was designed. A rigid linker was introduced to ensure more efficient conjugation of the aromatic ring π systems by limiting rotational freedom. The resulting fluorenol (9-hydroxyfluorene)-based photocages had superior spectral properties to those of simple biphenyl systems. The best uncaging cross section achieved was 5320 m cm (ϵΦ ).

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“…Examples of synthetic procedures for selected key compounds are given in the following text. Synthetic details for other compounds can be found in the Supporting Information …”

Section: Methodsmentioning

confidence: 99%

Section: Organic Synthesismentioning

confidence: 99%

A New Photocage Derived from Fluorene

Reinfelds

Cosel

Falahati

et al. 2018

Chemistry A European J

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“…It has been utilized in catalyst recovery, synthesis of metal complexes, purification of gas oil, self‐assembly, synthesis of soft materials, etc. Earlier the strategy was to synthesize 2 from fluorenone via nitration using mixed acid . This made the synthesis somewhat costly.…”

Section: Resultsmentioning

confidence: 99%

2,4,7‐Triaminofluorenone as a Multi‐Analyte Colorimetric Sensor of Fluoride, Acetone Vapor, and Other Harmful Compounds

Mohar

2019

ChemistrySelect

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2,4,7‐Triaminofluorenone, a fluorenone derived multi‐analyte colorimetric chemosensor, has been synthesized via an extremely cost‐effective synthetic pathway. The sensor molecule can detect various analytes such as fluoride ion, acetone vapor, and picric acid. The violet solution of the sensor molecule becomes deep blue in the presence of fluoride ion. It can detect fluoride down to 120 ppb level. The compound in the solid state shows vapochromism only in the presence of acetone. The grey colored solid coating of the sensor molecule becomes blue in the presence of acetone vapor. This property was utilized to sense acetone vapor. Color Grab, an android based app, was utilized to detect acetone in real time down to 10 ppm level. Apart from that, the same sensor molecule was also tested for sensing different electron deficient nitro aromatic compounds due to its electron rich framework. The sensor was found to detect picric acid selectively. The sensor compound also shows acid‐base induced color change. The violet solution of the sensor molecule becomes brown in the presence of carboxylic as well as mineral acid. This reaction is reversible. Hence, the brown solution becomes violet again in the presence of aliphatic amines as well as ammonia. Utilizing this property, a method has been described to detect two widely used highly volatile chemicals HCl and NH3 in different industries.

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“…Trinitrotoluene (TNT) and 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX) were obtained from Austin Explosive, Austin, TX, with purity of 99%. (E)-4-(4-nitrostyryl)-N,N-diphenylaniline (NSDPA), biphenyl-4-carboxylic acid (BCA), 2,4,7-trinitrofluorenone (TNF), and 2,7-dibromo-4-nitrofluorenone (DBNF) were synthesized from literature protocols, with purity of 99% (the experimental details and characterization data for these four compounds are given in ESI) [37][38][39][40]. Nitrocellulose (NC; 4-8% in ethanol/diethyl ether), carbazole (>95%), hexadecyl-trimethylammonium bromide (CTAB; 99%), tetra-n-butylammonium bromide (TBAB; 99%), didecyldimethylammonium bromide (99%), naphthalene (99%), poly(methyl methacrylate) (PMMA, average Mn = 10,400), polystyrene (PS, average Mn = 4020), and poly(dimethylsiloxane) (PDMS, average Mn = 4020) used for this study were purchased from SigmaAldrich Inc. Al (99.999%), Au (99.99%), Cu (99.99%), Cr (99.998%), and Ni (99.995%) are purchased from Kurt J. Lesker Company.…”

Section: Methodsmentioning

confidence: 99%