2595-90-6

Usage

Uses

Used in Chemical Synthesis:
3-(Bromomethyl)pyrene is used as a key intermediate in the synthesis of fluorophores for the fluorescent sensing of a variety of analytes. This includes metal ions such as Cd2+ and Zn2+, as well as adenosine triphosphate (ATP) sensing at physiological pH. Its ability to form stable and selective complexes with these analytes makes it a valuable tool in the development of sensitive and accurate detection methods.
Used in Photoinitiator Synthesis:
In the field of polymer chemistry, 3-(Bromomethyl)pyrene is used as a starting material for the synthesis of photoinitiators (PIs). These photoinitiators are essential for the radical polymerization of acrylates and the cationic polymerization of epoxy-silicone and vinyl ethers. The use of 3-(Bromomethyl)pyrene in the production of PIs allows for the creation of materials with improved properties, such as enhanced durability and resistance to environmental factors.
Used in Analytical Chemistry:
3-(Bromomethyl)pyrene is also employed in the development of analytical methods for the detection and quantification of various analytes. Its unique chemical properties enable the design of highly selective and sensitive fluorophores, which can be used in a range of applications, from environmental monitoring to medical diagnostics.
Used in Polymer Industry:
In the polymer industry, 3-(Bromomethyl)pyrene is used as a precursor for the synthesis of photoinitiators that are crucial for the polymerization of various monomers. The resulting polymers find applications in a wide range of industries, including automotive, aerospace, electronics, and packaging, due to their improved mechanical, thermal, and chemical properties.

InChI:InChI=1/C17H11Br/c18-10-14-7-6-13-5-4-11-2-1-3-12-8-9-15(14)17(13)16(11)12/h1-9H,10H2

Upstream product

• 67-56-1 methanol 
• 129-00-0 pyrene 
• 24463-15-8 1-pyrenemethanol 
• 3029-19-4 pyrene-1-aldehyde 
• 2381-21-7 1-methylpyrene 

Downstream Products

• 33895-37-3 pyren-1-ylmethyltriphenylphosphonium bromide 
• 38801-65-9 dimethyl(4-pyren-1-ylphenyl)amine 
• 80525-75-3 Dimethyl-[4-((E)-2-pyren-1-yl-vinyl)-phenyl]-amine 
• 1067915-18-7 methylpyrenyl p-methoxyphenyl sulfide 
• 1067915-12-1 1-methylpyrenyl phenyl sulfide 
• 176650-98-9 3-(1-pyrenylmethyloxy)benzyl alcohol 
• 1621327-45-4 (S)-3-butyl-2,2-dimethyl-5-[4-(pyren-1-ylmethoxy)-benzyl]imidazolidin-4-one 
• 17088-21-0 1-vinylpyrene 

Relevant academic research and scientific papers

Undulation induced tuning of electron acceptance by edge-oxidized graphene oxide

Edge-oxidized graphene oxide (EOGO) nanosheets are good acceptors of electrons. We have employed a suitably designed pyrene-tailed fluorescent probe to establish that the electron acceptability of EOGO can be tuned by undulation of the GO sheet. Comparison between EOGO and single-walled carbon nanotubes (SWCNT) on electron acceptance from the probe molecule shows that the efficiency of π-π stacking between pyrene and the graphene sheet plays the key role.

A facile approach for sensitive, reversible and ratiometric detection of biothiols based on thymine-mediated excimer-monomer transformation

A ratiometric fluorescent sensor was developed for detecting biothiols in water and biological samples such as urine and serum. For this sensor, the monomer-excimer emission variations were regulated by aggregation and deaggregation via the complexation between pyrene-thymine and mercury ions modulated by biothiols.

Complexation of metal ions with the novel diazadithia crown ethers carrying two pyrene pendants in acetonitrile-tetrahydrofuran

Two crown ethers carrying pyrene side arms with nitrogen-sulfur donor atom were designed and synthesized by the reaction of the corresponding macrocyclic compounds and 1-bromomethyl-pyrene. The influence of metal cations such as Al3+, Zn2+, Fe2+, Fe3+, Co2+, Ni2+, Mn2+, Cu2+, Cd2+, Hg2+ and Pb2+ on the spectroscopic properties of the ligands was investigated in acetonitrile-tetrahydrofuran (1:1) by means of absorption and emission spectrometry. Absorption spectra show isosbestic points in the spectrophotometric titration of Al3+, Zn2+, Fe2+, Ni2+, Cu2+, and Pb2+ with 16-membered crown ether. Similar results were obtained for Al3+, Fe2+, Hg2+, Cu2+ and Pb2+ with 14-membered crown ether. The results of spectrophotometric titration experiments disclosed the complexation stoichiometry and complex stability constants of the novel ligands with these cations. According to spectrofluorimetric titration measurements the 14-membered diazadithia crown ether showed sensitivity for Pb2+ with linear range and detection limit of 1.3 × 10-6 to 5.2 × 10-5 M and 5.2 × 10-7 M, respectively. The 16-membered diazadithia crown ether showed sensitivity for Ni2+ with linear range and detection limit of 1.3 × 10-7 to 5.2 × 10-6 M and 4.1 × 10-8 M, respectively.

Supramolecular peptide amphiphile vesicles through host-guest complexation

Tricky triggering: Supramolecular peptide amphiphiles were prepared by host-guest complexation of pyrene-labeled peptides and viologen lipid with cucurbit[8]uril. They self-assemble into vesicles, which are responsive to a variety of external triggers. Both "switching on" and "switching off" of fluoresence and cytotoxicity is demonstrated in vitro. Copyright

Pyrene-imidazolium complexed graphene for the selective fluorescent detection of G-quadruplex forming DNA

A unique system has been developed for quantifying G-quadruplex forming DNA down to picomolar levels for future applications in telomeric assessment. Pyrene-imidazolium captured in high amounts on the surface of reduced graphene oxide shells allows specific DNA sequence detection by complex formation resulting in release and fluorescence enhancement of pyrene-imidazolium.

Selective recognition of ATP by multivalent nano-assemblies of bisimidazolium amphiphiles through “turn-on” fluorescence response

Bisimidazolium receptors, tagged with chromophoric pyrene at one end and linked to an n-alkyl chain at the other, underwent self-assembly in aqueous media depending on the length of the alkyl segment. The amphiphilic derivatives having n-decyl or longer chains, formed nano-assemblies with cyanic-green emission resulting from the stacked pyrene chromophores in the aggregates. The presence of positive surface charges on the multivalent aggregates led to ATP binding which was accompanied by a significant increase in the excimeric emission intensity. This provided a convenient way of monitoring ATP binding in a “turn-on” mode and an efficient detection of ATP was achieved in aqueous buffer and also in buffer containing 150 mM NaCl at physiological pH value. Furthermore, the multivalent aggregates demonstrated a significant selectivity in ATP detection over ADP, AMP and pyrophosphate.

DNA interaction of a fluorescent, cytotoxic pyridinimino platinum(II) complex

New pyridinimino complexes of platinum(II) [PtCl2(N^N-R)] (N^N = 2-pyridylmethanimino, R = -(CH2)2O(CH2)2OH, -(CH)2O(CH2)2OCH2Pyr), Pyr = pyren-1-yl) have been prepared. They are characterized by a dioxygenated alkyl side chain and, in one case, by a fluorescent terminal 1-pyrenyl residue. The complexes were characterized by elemental analysis, IR, 1H–, 13C–and 195Pt NMR spectroscopies. For [PtCl2(N^N-(CH2)2O(CH2)2OH] the molecular structure was determined by single crystal X-ray diffraction. The complexes are soluble and stable in DMSO/H2O (80/20, v/v). The pyrenyl terminated compound was tested as antiproliferative agent against selected human cancer cell lines. Comparable cytotoxic effect was obtained on human ovarian carcinoma A-2780 and A-2780cis cells, thus suggesting a certain ability to circumvent cisplatin resistance. The interaction of this complex with DNA was investigated by linear flow dichroism and by spectrophotometric (absorbance and fluorescence) titrations. Both techniques enlightened the presence of a complex mode of interaction with DNA, involving both groove binding and intercalation.

Spacer length effect on the photoinduced electron transfer fluorescent probe for alkali metal ions

We have synthesized four derivatives of alkyl pyrene covalently bonded to aza-18-crown-6 at the nitrogen position, Py(CH2)n, (n = 1-4), to study the effect of spacer length on the emission properties of pyrene fluorophore upon complexation of alkali metal ions by the crown moiety. In the absence of alkali metal ions, the parent molecule is weakly fluorescent because its emission is partially quenched by photoinduced electron transfer (PET) from nitrogen lone pairs to the excited singlet state of pyrene. Complexation of alkali metal ions (e.g. K+) by the crown moiety prevents the nitrogen lone pair from participating in PET and results in an enhancement in the observed emission from pyrene (fluorescent turn on). Because the PET effect could be exerted through bonds as well as space, its magnitude may show a dependence on chain length. We have examined the fluorescence behavior of these pyrene aza-crown ether derivatives in the presence of alkali metal ions to determine the magnitude of such an effect and its impact on the sensitivity of the fluorescent probe for detection purposes. Our results indicate that maximum efficiency for PET between the pyrene moiety and aza-crown ether is achieved when n ≤ 3.

Investigations on nanoparticle-chromophore and interchromophore interactions in pyrene-capped gold nanoparticles

Three pyrene alkanethiol derivatives (P1, P2, and P3) possessing flexible alkyl groups of different lengths were attached to nanoparticles of gold (a??2-3 nm in size) along with dodecanethiol (Au-Pl, Au-P2, and Au-P3). The photophysical properties of these systems were investigated as a function of (i) distance of chromophore from gold core, (ii) concentration of pyrene on gold surface, and (iii) solvent polarity. The structured absorption bands of the pyrene chromophore were significantly perturbed near the surface of gold nanoparticles (Au-Pl), indicating a strong ground state interaction between the plasmon electrons of Au nanoparticles and the ??-electron cloud of the chromophore. Such effects were not observed in Au-P2 and Au-P3 systems, in which the linker groups are long enough to prevent any ground state interactions. A gradual increase in the peak intensity ratio of band III/I of the normal fluorescence of pyrene chromophore was found with an increase in length of the spacer group. These results indicate that the local environment close to the surface of the Au nanoparticle is more polar compared to the bulk medium. Interchromophoric interactions are limited in the Au-P1 system due to the restriction imposed by the curvature of spherical gold nanoparticle whereas the flexible alkyl chain tethering pyrene in Au-P2/Au-P3 allows free interaction between chromophores. Steady state and time-resolved emission studies indicate that the normal fluorescence and intermolecular excimer formation are the main deactivation channels of the singlet excited state of pyrene linked to Au nanoparticles, in nonpolar solvents. In contrast, the competitive electron transfer to the gold nanocore dominates in polar solvents.

Unique sandwich stacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH

A pincer-like benzene-bridged sensor 1 with a pyrene excimer as a signal source and imidazolium as a phosphate anion receptor was synthesized and investigated for ATP sensing. A unique switch of excimer vs monomer pyrene fluorescence of 1 is observed in the presence of ATP due to the charcteristic sandwich π-π stacking of pyrene-adenine-pyrene. On the other hand, four other bases of nucleoside triphosphates such as GTP, CTP, UTP, and TTP can interact only from the outside with the already stabilized stacked pyrene-pyrene dimer of 1, resulting in excimer fluorescence quenching. The fluorescent intensity ratio of monomer-to-excimer for 1 upon binding with ATP (I 375/I487) is much larger than that upon binding with ADP and AMP. This difference is large enough to discriminate ATP from ADP and AMP. As one of the biological applications, sensor 1 is successfully applied to the ATP staining experiments. Sensor 1 is also applied to monitor the hydrolysis of ATP and ADP by apyrase. The results indicate that 1 is a useful fluorescent sensor for investigations of ATP-relevant biological processes.