944940-91-4

Upstream product

• 302579-16-4 2-bromo-7-N,N’-diphenylamino-9,9’-dimethyl-9H-fluorene 
• 68-12-2 N,N-dimethyl-formamide 
• 122-39-4 diphenylamine 
• 944940-90-3 7-bromo-9,9-dimethyl-9H-fluorene-2-carbaldehyde 
• 28320-32-3 2,7-dibromo-9,9-dimethyl-9H-fluorene 

Downstream Products

• 1430205-01-8 5-(2-(7-(diphenylamino)-9,9-dimethyl-fluoren-2-yl)benzothiazol-6-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol 
• 1430205-04-1 (2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(2-(7-(diphenylamino)-9,9-dimethyl-9H-fluoren-2-yl)benzo[d]thiazol-6-yl)tetrahydrofuran-3-ol 
• 1430204-99-1 7-(6-bromobenzothiazol-2-yl)-9,9-dimethyl-N,N-diphenyl-fluoren-2-amine 

Relevant academic research and scientific papers

A photoelectric conversion element and its method of use, a light sensor, an imaging element

PROBLEM TO BE SOLVED: To provide a photoelectric conversion element exhibiting excellent photoelectric conversion efficiency and low dark current properties in the case of heat treatment being performed.SOLUTION: The photoelectric conversion element includes, in the given order, a conductive film, a photoelectric conversion film containing a photoelectric conversion material, and a transparent conductive film. The photoelectric conversion material contains a compound (A) represented by formula (1).

Erratum: Genetically encoded multispectral labeling of proteins with polyfluorophores on a DNA backbone (Journal of the American Chemical Society (2013) 135 (6184-6191) DOI: 10.1021/ja4004393)

A n internal review of our NMR data in the published Supporting Information (SI) file revealed that one of the authors (V.S.) had digitally removed peaks of impurities and solvents from some of the spectra. To correct this, we now provide a new version of the SI file with the unaltered spectra. Two new authors (K.M.C., S.A.C.) have recharacterized the original haloalkyl reagent B8 and have confirmed its identity by NMR and mass spectrometry. In addition, we have confirmed the identity of one of the original dyes by MALDI-TOF mass spectrometry, and used it successfully to label bacteria expressing a HaloTag fusion; these data are added to the corrected SI file. We stand by the conclusions of the article, and we regret the publication of the altered characterization data. We also correct the author list to include the scientists (K.M.C. and S.A.C.) who worked to independently check the data and conclusions. The new author list should read as follows: Vijay Singh, Shenliang Wang, Ke Min Chan, Spencer A. Clark, and Eric T. Kool.

Spirobifluorene based small push-pull molecules for organic photovoltaic applications

Four analogous push-pull systems have been synthesized. If the latter all involve the same electron rich diphenylamine termination (D) and π-conjugating spacer (p) they differ from their electron withdrawing groups (A) and more importantly by their linear or 3D structure. Indeed, two push-pull spirobifluorene derivatives, which present two perpendicular D-p-A systems by molecule, are compared to their linear analogues. After description of their syntheses, spectroscopic and electrochemical properties, comforted by theoretical calculations, are discussed and compared. Then, a preliminary evaluation of compounds as active materials in organic solar cells is presented and demonstrates the potential interest of spiro-based derivatives for organic photovoltaics.

Design, synthesis and properties of near-infrared molecular switches containing a fluorene ring

Three molecular switches containing a fluorene ring were designed and synthesized. The introduction of the amino group substituted fluorene ring resulted in the target molecular switches having some optical properties in the near-infrared region. It was demonstrated that the N-substituents on the fluorene rings and the switch units both had great influence on the molecular switch optical properties including the absorption maximum, absorption intensity and fluorescence quantum yield. The open-ring forms IA and IIA showed obvious solvatochromic behaviour. The closed-ring forms IIB and IIIB showed obvious hydrochromic behaviour in MeCN/water binary solvent systems and acidichromic behaviour in MeCN solution with high reversibility. Especially, the distinct off-on fluorescence signal in the near-infrared region using the stimuli of acid means that the designed compounds have great potential application value in the field of biological sensing.

Genetically encoded multispectral labeling of proteins with polyfluorophores on a DNA backbone

Genetically encoded methods for protein conjugation are of high importance as biological tools. Here we describe the development of a new class of dyes for genetically encoded tagging that add new capabilities for protein reporting and detection via HaloTag methodology. Oligodeoxyfluorosides (ODFs) are short DNA-like oligomers in which the natural nucleic acid bases are replaced by interacting fluorescent chromophores, yielding a broad range of emission colors using a single excitation wavelength. We describe the development of an alkyl halide dehalogenase-compatible chloroalkane linker phosphoramidite derivative that enables the rapid automated synthesis of many possible dyes for protein conjugation. Experiments to test the enzymatic self-conjugation of nine different DNA-like dyes to proteins with HaloTag domains in vitro were performed, and the data confirmed the rapid and efficient covalent labeling of the proteins. Notably, a number of the ODF dyes were found to increase in brightness or change color upon protein conjugation. Tests in mammalian cellular settings revealed that the dyes are functional in multiple cellular contexts, both on the cell surface and within the cytoplasm, allowing protein localization to be imaged in live cells by epifluorescence and laser confocal microscopy.