136039-69-5

Usage

Structure

A central benzene ring with two benzoyl groups attached at the 1 and 3 positions, each substituted with a bromine atom.

Derivative of

Benzophenone

Applications

a. Organic synthesis
b. Building block for various organic compounds
c. Manufacturing of pharmaceuticals and agrochemicals
d. Production of organic light-emitting diodes (OLEDs) and organic semiconductors

Potential

As a photoresponsive material

Investigated for

Photocrosslinkable properties in the development of photoactive polymers and materials.

Upstream product

• 108-86-1 bromobenzene 
• 99-63-8 benzene-1,3-dicarbonyl dichloride 

Downstream Products

• 1198211-93-6 1,3-bis(9-(4-bromophenyl)-9H-fluoren-9-yl)benzene 
• 1253788-94-1 4,4’-(9,9’-(1,3-phenylene)bis(9H-fluorene-9,9'-diyl))bis(N,N-diphenylaniline) 
• 1253788-95-2 N,N'-(4,4'-(9,9'-(1,3-phenylene)bis(9H-fluorene-9,9-diyl))bis(4,1-phenylene))bis(N-phenylnaphthalen-1-amine) 
• 1458033-46-9 1,3-bis(4-bromobenzoyl)benzene bis-thiosemicarbazone 

Relevant academic research and scientific papers

Synthesis and biochemical evaluation of benzoylbenzophenone thiosemicarbazone analogues as potent and selective inhibitors of cathepsin L

Upregulation of cathepsin L in a variety of tumors and its ability to promote cancer cell invasion and migration through degradation of the extracellular matrix suggest that cathepsin L is a promising biological target for the development of anti-metastatic agents. Based on encouraging results from studies on benzophenone thiosemicarbazone cathepsin inhibitors, a series of fourteen benzoylbenzophenone thiosemicarbazone analogues were designed, synthesized, and evaluated for their inhibitory activity against cathepsins L and B. Thiosemicarbazone inhibitors 3-benzoylbenzophenone thiosemicarbazone 1, 1,3-bis(4-fluorobenzoyl)benzene thiosemicarbazone 8, and 1,3-bis(2-fluorobenzoyl)-5-bromobenzene thiosemicarbazone 32 displayed the greatest potency against cathepsin L with low IC50 values of 9.9 nM, 14.4 nM, and 8.1 nM, respectively. The benzoylbenzophenone thiosemicarbazone analogues evaluated were selective in their inhibition of cathepsin L compared to cathepsin B. Thiosemicarbazone analogue 32 inhibited invasion through Matrigel of MDA-MB-231 breast cancer cells by 70% at 10 μM. Thiosemicarbazone analogue 8 significantly inhibited the invasive potential of PC-3ML prostate cancer cells by 92% at 5 μM. The most active cathepsin L inhibitors from this benzoylbenzophenone thiosemicarbazone series (1, 8, and 32) displayed low cytotoxicity toward normal primary cells [in this case human umbilical vein endothelial cells (HUVECs)]. In an initial in vivo study, 3-benzoylbenzophenone thiosemicarbazone (1) was well-tolerated in a CDF1 mouse model bearing an implanted C3H mammary carcinoma, and showed efficacy in tumor growth delay. Low cytotoxicity, inhibition of cell invasion, and in vivo tolerability are desirable characteristics for anti-metastatic agents functioning through an inhibition of cathepsin L. Active members of this structurally diverse group of benzoylbenzophenone thiosemicarbazone cathepsin L inhibitors show promise as potential anti-metastatic, pre-clinical drug candidates.

Luminous butterflies: Efficient exciton harvesting by benzophenone derivatives for full-color delayed fluorescence OLEDs

Butterfly-shaped luminescent benzophenone derivatives with small energy gaps between their singlet and triplet excited states are used to achieve efficient full-color delayed fluorescence. Organic light-emitting diodes (OLEDs) with these benzophenone deri

COMPOSITIONS AND METHODS FOR INHIBITION OF CATHEPSINS

This invention is directed to compound of Formula I and methods of using these compounds in the treatment of conditions in which modulation of a cathepsin, particularly cathepsin K or cathepsin L, will be therapeutically useful.

Phenyl-substituted fluorene-dimer cored anthracene derivatives: Highly fluorescent and stable materials for high performance organic blue- and white-light-emitting diodes

A new series of highly fluorescent blue-emitting materials based on fluorene and anthracene hybrids are designed and synthesized for organic light-emitting diodes (OLEDs). These materials feature a phenyl-substituted fluorene dimer as a bulky and rigid core and anthracene as a functional active group. The novel use of a phenyl-substituted fluorene dimer as building skeleton to design functional molecules is reported for the first time. The thermal, photophysical, electrochemical, and electroluminescent (EL) properties are presented, as well as combined density functional study of their geometry and electronic structure. These compounds show excellent thermal resistance with high glass transition temperature (Tg) in the range 159-257°C, thermal decomposition temperature (Td) 441-495°C, and high fluorescent quantum yield (ΦF = 0.61-0.96, relative to 9,10-diphenylanthracene) as well as good film-forming and morphological stability. Remarkably, high-performance blue OLEDs are also fabricated in a simple three-layer device architecture using these compounds as emissive layer with luminance efficiency of 2.2-5.1 cd A-1 as a non-doped blue emitter and even higher efficiency of up to 13.6 cd A-1 and maximum external quantum efficiency 4.8% is obtained when doped a blue fluorescent dye, 4,4′-(1E,1′E)-2,2′(biphenyl-4,4′diyl)bis(ethane-2, 1-diyl)bis(N,N-dip-tolyaniline) (DPAVBi). Furthermore, we fabricate highly efficient fluorescent white OLEDs employing an interesting emission in the longer wavelength of one of our compound combined with DPAVBi emission to achieve stable white light emission in a binary blend single emissive layer with high efficiency of 14.8 cd A-1 (5.3 lm W-1) and maximum brightness of 50248 cd m-2.

An alternative approach to constructing solution processable multifunctional materials: Their structure, properties, and application in high-performance organic light-emitting diodes

A new series of full hydrocarbons, namely 4,4'-(9,9'-(1,3-phenylene) bis(9H-fluorene-9,9-diyl))bis(N,N-diphenylaniline) (DTPAFB), N,N'-(4,4'- (9,9'-(1,3-phenylene)bis(9H-fluorene-9,9-diyl))bis(4,1-phenylene))bis(N^ phenylnaphthalen-1-amine) (DNPAFB), 1,3-bis(9-(4-(9H-carbazol-9-yl) phenyl)-9H-fluoren-9-yl)benzene, and 1,3-bis(9-(4-(3,6-di-tert-butyl-9H- carbazol-9-yl)phenyl)-9H-fluoren-9-yl)benzene, featuring a highly twisted tetra- hedral conformation, are designed and synthesized. Organic light-emitting diodes (OLEDs) comprising DNPAFB and DTPAFB as hole transporting layers and tris(quinolin-8-yloxy)aluminum as an emitter are made either by vacuum deposition or by solution processing, and show much higher maximum efficiencies than the commonly used N,N'-di(naphthalen-1-yl)-N,N'- diphenylbiphenyl-4,4'- diamine device (3.6 cd A-1) of 7.0 cd A-1 and 6.9 cd A-1, respectively. In addition, the solution processed blue phosphorescent OLEDs employing the synthesized materials as hosts and iridium (III) bis[(4,6-di- fluorophenyl)-pyridinato-N, C2] picolinate (FIrpic) phosphor as an emitter present exciting results. For example, the DTPAFB device exhibits a brightness of 47 902 cd m-2, a maximum luminescent efficiency of 24.3 cd A-1, and a power efficiency of 13.0 lm W-1. These results show that the devices are among the best solution processable blue phosphorescent OLEDs based on small molecules. Moreover, a new approach to constructing solution processable small molecules is proposed based on rigid and bulky fluorene and carbazole moieties combined in a highly twisted configuration, resulting in excellent solubility as well as chemical miscibility, without the need to introduce any solubilizing group such as an alkyl or alkoxy chain.