70173-54-5

Usage

Chemical Properties

White Crystalline

InChI:InChI=1/C12H14BrN/c13-11-7-9-3-1-5-14-6-2-4-10(8-11)12(9)14/h7-8H,1-6H2

Upstream product

• 479-59-4 julolidine 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 76859-18-2 N-crotyljulolidinium bromide 
• 93033-85-3 4-Allyl-9-bromo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolinium; bromide 

Downstream Products

• 89375-11-1 1,2-Bis-(julolidyl)-ethan-1,2-dion 
• 201533-79-1 [4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)benzylidene]propanedinitrile 
• 1352574-11-8 4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)benzaldehyde 

Relevant academic research and scientific papers

Influence of different acceptor groups in julolidine-based organic dye-sensitized solar cells

Two novel organic dyes containing julolidine as the electron donor and cyanoacetic acid or rhodanine-3-acetic acid as the electron acceptor bridged by bithiophene unit were synthesized. The absorption spectra, electrochemical and photovoltaic properties of the new dyes were extensively investigated. Transient absorption spectra measurements show that both sensitizers are quickly regenerated and the dye cations are efficiently intercepted by the redox mediator. The overall conversion efficiencies of 2.6% and 2.0% were obtained for dye-sensitized solar cells (DSSC) based on the cyanoacetic acid and rhodanine derived dyes, respectively. Compared with the rhodanine terminated dye, the open circuit voltage and the conversion efficiency of solar cell based on the cyanoacetic acid dye are increased about 25% and 30%, respectively. The lower efficiency of solar cell based on rhodanine is mainly resulted from the broken delocalization of the excited state due to the NCH2CO2H anchor, which affects the electron injection from the rhodanine terminated dye to the conduction band of TiO2.

HOLE TRANSFER MATERIAL, INORGANIC-ORGANIC HYBRID SOLAR CELL USING THE SAME, AND THE MANUFACTURING METHOD THEREOF

Disclosed is a compound represented by chemical formula 1 for hole transfer. Also, disclosed is an inorganic-organic hybrid solar cell comprising a first electrode, a semiconductor layer, a light absorption layer, a hole transfer layer, and a second elect

Thiophene-inserted aryl-dicyanovinyl compounds: The second generation of fluorescent molecular rotors with significantly redshifted emission and large stokes shift

Fluorescent molecular rotors can be used as molecular sensors for the viscosity of a microenvironment. However, these molecular rotors are limited to 9-(dicyanovinyl)julolidine (DCVJ) and a few derivatives. Furthermore, these traditional rotors show short absorption/emission wavelengths and small Stokes shifts. To address these drawbacks, we have developed a small library of new molecular rotors for viscosity sensing, prepared by incorporating a thiophene unit into the conventional fluorescent molecular rotors with the aim of accessing molecular rotors with redshifted excitation/emission wavelengths and larger Stokes shifts compared with the known rotors. The new rotors show substantially improved photophysical properties. For example, rotor 4 shows absorption/emission wavelengths of 559/697 nm, respectively, and a very large Stokes shift of 138 nm compared with the absorption/emission wavelengths (465/503 nm) and very small Stokes shift (38 nm) of the traditional fluorescent molecular rotor DCVJ. The photophysical properties of the rotors were rationalized by DFT calculations. Thiophene-inserted aryl-dicyanovinyl molecular rotors were prepared that show substantially improved photophysical properties for the absorption/emission wavelengths and the Stokes shift. For example, rotor 4 shows absorption/emission wavelengths of 559/697 nm, respectively, and a very large Stokes shift of 138 nm compared with the traditional molecular rotor DCVJ.

Electrophilicities of symmetrically substituted 1,3-diarylallyl cations

Kinetics of the reactions of nine symmetrically substituted 1,3-diarylallyl cations with different nucleophiles were studied photometrically in dichloromethane, acetonitrile, and DMSO solutions. The second-order rate constants k2 were found to follow the correlation log k2 = sN(N + E). The electrophilicity parameters E of the title cations were derived, using the known values of sN and N of the nucleophilic reaction partners, and compared with the electrophilicities of analogously substituted benzhydrylium ions. Good linear correlations were found between the electrophilicities E and the quantum chemically calculated gas-phase methyl anion affinities of the allyl cations and the σ+ constants of the substituents X.

New intramolecular through-space charge transfer emission: Tunable dual fluorescence of terfluorenes

We have synthesized a series of new terfluorene derivatives, and investigated their novel fluorescence emission behaviors. We have demonstrated a new intramolecular through-space charge transfer emission experimentally and theoretically. This is the first

Synthesis of arylbromides from arenes and Nbromosuccinimide bromosuccinimide (NBS) in acetonitrile - A convenient method for aromatic bromination

Regioselective and chemoselective electrophilic bromination of a wide series of activated arenes using N-bromosuccinimide (NBS) in acetonitrile occurs readily. Environmentally friendly conditions, large substrate scope, and ease of synthesis enhance the utility of this method over other electrophilic bromination conditions.

The influence of tetrahydroquinoline rings in dicyanomethylenedihydrofuran (DCDHF) single-molecule fluorophores

We have synthesized several series of DCDHF fluorophores with the amine donor either acyclic or constrained in one or two tetrahydroquinoline rings. The absorption and the fluorescence emission wavelengths and quantum yields have been determined and correlated with the specific donor structures. Generally, inclusion of the donor in a ring annulated to the benzene or naphthalene aromatic (Ar) π-core results in a bathochromic shift of absorption and emission accompanied by an increase in the quantum yield. Thus, the tetrahydroquinoline donor provides an efficient way to tailor the properties of fluorophores with substituted amines as electron-donating groups.

Amino-Claisen Rearrangement. IV. Quaternary Amino-Claisen Rearrangement of N-Allyljulolidinium Derivatives

The amino-Claisen rearrangements of 9-unsubstituted and 9-substituted N-allyljulolidinium halides were investigated.The former compounds can be regarded as aniline derivatives in which the two ortho sites are occupied.In the latter compounds, the two ortho positions and the para position are all blocked.N-Allyljulolidinium halides rearranged into 9-allyljulolidine.However, 9-substituted N-allyljulolidinium halides gave 8-allyl-9-substituted julolidines.This meta rearrangement constitutes the first reported example of meta amino-Claisen rearrangement.The reaction pathways can be rationalized in terms of a combination of and sigmatropic rearrangements.Keywords - amino-Claisen rearrangement; meta-rearrangement; N-allyljulolidinium halide; 9-substituted-N-allyljulolidinium halide; 9-allyljulolidine; 8-allyl-9-substituted julolidine; sigmatropic rearrangement; sigmatropic rearrangement

Novel synthesis of 3,3-substituted dihydrobenzisothiazole-1,1-dioxides and -2,3-dihydronaphtho-1,2-thiazine-1,1-dioxides

This invention relates to a method of synthesizing certain 3-(carbocyclic aryl)-3-(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) by reacting (a) a 4-OP-carbocyclic aryllithium compound wherein P is a protecting group and (b) a 3-(carbocyclic aryl)benz[d]isothiazole-1,1-dioxide wherein said 3-(carbocyclic aryl) moiety is other than a 3-(4'-OP-carbocyclic aryl) moiety to give (c) the corresponding 3-carbocyclic aryl)-3-(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide. The -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides are prepared in the same manner by reacting a 3-(carbocyclic aryl)naphtho[1,8-de]-1,2-thiazine-1,1-dioxide with said 4'-OP-carbocyclic aryllithium compound. In a further embodiment, the compounds synthesized according to the foregoing method are reacted with a carboxylic acid halide to give the corresponding 2-carbonyl-substituted 2,3-dihydrobenz[d]isothiazole-1,1-dioxide (or -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) followed by removing the protecting group, P, with weak acid to yield certain phenol and 1-naphthol sulfam(na)phthaleins useful, e.g., as optical filter agents and filter agent precursors in photography.

3-(Julolidinyl)-benz[d]isothiazole-1,1-dioxide

This invention relates to 3-(julolidinyl)-benz[d]-isothiazole-1,1-dioxide useful as an intermediate in the synthesis of certain 3,3-disubstituted-2,3-dihydrobenz[d]-isothiazole-1,1-dioxide dyes which find utility as, for example, photographic optical filter agents and filter agent precursors.