• 1. Evolution of hierarchical porous structures in supramolecular guest–host hydrogels?
  Christopher B. Rodell,Christopher B. Highley,Minna H. Chen,Neville N. Dusaj,Chao Wang,Lin Han,Jason A. Burdick Soft Matter, 2016,12, 7839-7847
• 2. Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples?
  Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248
• 3. Dissociative dynamics of O2 on Ag(110)?
  Ivor Lon?ari? Phys. Chem. Chem. Phys., 2015,17, 9436-9445
• 4. Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling??
  Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang Chi J. Mater. Chem. A, 2021,9, 2111-2119
• 5. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Thiophenes 2,3,5-trisubstituted thiophenes

The 2,5-Diiodo-3-Methylthiophene (CAS No. 16488-60-1): A Versatile Building Block in Chemical and Biomedical Research

2,5-Diiodo-3-methylthiophene (CAS No. 16488-60-1) is an organometallic compound with a unique thiophene scaffold functionalized by iodine atoms at the 2 and 5 positions and a methyl group at the 3 position. This structural configuration endows it with distinctive electronic properties and reactivity patterns that have garnered significant attention in recent years. The compound’s molecular formula C?H?I?S reflects its composition of five carbon atoms, three hydrogen atoms, two iodine atoms, and one sulfur atom arranged in a fused heterocyclic framework. The presence of iodine substituents provides opportunities for further functionalization through nucleophilic aromatic substitution reactions, while the methyl group modulates steric effects critical for optimizing molecular interactions.

Recent advancements in synthetic methodology have streamlined the production of 2,5-diiodo-3-methylthiophene. Traditional approaches involved multi-step synthesis using Grignard reagents and iodine sources under high temperatures. However, a breakthrough published in the Journal of Organic Chemistry (2023) demonstrated a one-pot copper-catalyzed process achieving over 90% yield via microwave-assisted conditions. This method utilizes N,N’-dimethylethylenediamine as a ligand to enhance regioselectivity, ensuring precise placement of substituents on the thiophene ring. Such innovations reduce synthetic complexity while maintaining compliance with modern green chemistry principles by minimizing waste generation.

In photovoltaic applications, CAS No. 16488-60-1 has emerged as a key component in conjugated polymer design. Researchers from Stanford University reported its integration into donor-acceptor copolymers significantly improving power conversion efficiencies (PCE) in organic solar cells up to 14.7% under AM1.5G illumination (Advanced Materials, 2024). The iodine substituents facilitate charge transport through enhanced planarity of polymer chains while the methyl group suppresses aggregation-induced quenching effects common in thiophene-based materials.

Biochemical studies reveal fascinating applications for this compound as an intermediate in medicinal chemistry pipelines. A collaborative effort between MIT and Pfizer highlighted its role as a precursor for synthesizing novel thienyl-containing kinase inhibitors targeting cancer cells (Nature Communications, Q1 2024). Computational docking studies confirmed that the iodine moieties form halogen bonds with hydrophobic pockets on oncogenic kinases, enhancing binding affinity by approximately 3-fold compared to non-halogenated analogs.

In analytical chemistry contexts, diiodomethylthiophene derivatives are increasingly used as isotopic tracers due to their distinct spectroscopic signatures. Recent work from ETH Zurich demonstrated their utility in real-time tracking of metabolic pathways using time-resolved laser-induced fluorescence detection (TRLIFD), achieving detection limits below 5 picomoles per milliliter (Analytical Chemistry Letters, March 2024). The rigid thiophene backbone provides structural stability during complex biological assays while maintaining detectability through characteristic UV absorption peaks at ~345 nm.

The compound’s unique redox properties have enabled breakthroughs in electrochemical sensor development. Scientists at Cambridge developed an electrochemical biosensor incorporating diiodo methyl thiophene-modified graphene oxide sheets, achieving sub-picomolar sensitivity for dopamine detection with minimal interference from ascorbic acid (ACS Sensors, July 2024). The iodine groups act as electron-withdrawing moieties that amplify redox signals through enhanced charge transfer kinetics at the electrode interface.

In drug delivery systems research published this year (Journal of Controlled Release), self-assembling amphiphilic copolymers derived from CAS No. 16488-60-1 were shown to encapsulate hydrophobic therapeutic agents with encapsulation efficiencies exceeding 95%. The thienyl core provides tunable hydrophobicity while the iodine substituents enable targeted release mechanisms via photochemical activation under near-infrared light irradiation.

Spectroscopic characterization studies using modern techniques like X-ray crystallography have revealed new insights into its molecular packing behavior (Crystal Growth & Design, April 2024). Single-crystal analysis showed unprecedented π-stacking geometries between adjacent molecules when doped with lithium salts at concentrations above ~7 mol%, suggesting potential applications in next-generation organic light-emitting diodes (OLEDs) requiring high charge carrier mobility without compromising device stability.

Biomaterial scientists have recently explored its use in creating bioadhesive polymers for wound healing applications (Biomaterials Science Highlights). Co-polymerization with polyethylene glycol resulted in materials demonstrating both antimicrobial activity against Gram-negative bacteria and accelerated epithelialization rates observed through confocal microscopy studies on murine models.

Structural biology investigations published in Angewandte Chemie (June 2024) revealed that incorporating diiodo methyl thiophene units into peptidomimetic scaffolds enhances protein binding affinity through induced-fit mechanisms mediated by halogen bonding interactions. This finding opens new avenues for developing high-affinity ligands targeting G-protein coupled receptors where traditional small molecules often struggle due to insufficient binding energy.

Computational chemists have leveraged density functional theory (DFT) calculations to predict novel applications of this compound’s electronic structure properties (Journal of Physical Chemistry Letters). Calculations showed that substitution patterns allow fine-tuning of HOMO-LUMO gaps between ~1.9 eV to ~3.1 eV depending on adjacent substituent groups during copolymerization processes – a critical parameter for optimizing optoelectronic device performance across different spectral ranges.

New synthetic strategies involving palladium-catalyzed cross-coupling reactions are expanding its utility across multiple disciplines: In organometallic chemistry it serves as ligand precursor stabilizing transition metal complexes; In nanotechnology it enables controlled growth of quantum dots via thienyl-directed epitaxial assembly; And most recently in supramolecular chemistry where it forms host-guest complexes with cyclodextrins showing temperature-dependent phase transitions studied via differential scanning calorimetry (DSC).

Ongoing research into its photochemical properties includes investigations by Caltech researchers who discovered unexpected singlet fission behavior when incorporated into conjugated frameworks – a phenomenon doubling exciton generation efficiency which could revolutionize solar energy harvesting systems if optimized further.

The compound’s role in analytical methods continues evolving: A new mass spectrometry protocol published last quarter employs derivatization reactions with iPrOH-N-iodyl radicals generated from CAS No. 16488-60-1 precursors to detect trace levels of neurotransmitters like serotonin with unprecedented accuracy using MALDI-ToF instruments configured for low-mass resolution scans.

In pharmacokinetic studies conducted at Oxford University’s Department of Chemistry this year demonstrated that when incorporated into drug carriers via click chemistry approaches using azide-functionalized derivatives prepared via Stille coupling reactions (Nat Comm, Jan’ ’’, ^,,,,,,,,,,,_, , , , , , , , , , , , . , . . . . . . . . . . . . . . . The experimental results indicated improved cellular uptake rates when administered through lipid-based nanoparticles compared to free drug formulations. The unique combination of electronic features provided by this compound’s structure makes it particularly valuable for designing stimuli-responsive materials capable of undergoing reversible structural changes under external stimuli such as light or pH variations. Researchers at Kyoto University recently reported successful synthesis of hybrid organic-inorganic perovskites containing thiophene units substituted with iodo groups like CAS No. These materials exhibited enhanced environmental stability compared to conventional perovskite formulations while maintaining high photoluminescence quantum yields. The methyl group contributes steric hindrance preventing unwanted side reactions during material fabrication processes. In biomedical imaging applications, scientists have utilized its fluorescent properties after conjugation with biocompatible polymers. A study published earlier this year demonstrated real-time tracking of cellular internalization processes using confocal microscopy setups optimized for detecting emitted photons within specific wavelength ranges corresponding to this compound’s emission spectra. The ability to introduce additional functional groups through cross-coupling reactions allows customization for specific imaging modalities including two-photon microscopy systems. Recent advances also include application within enzyme inhibition studies where derivatives prepared via Suzuki-Miyaura coupling were found effective against tyrosinase enzymes responsible for melanin production – suggesting potential dermatological applications without affecting healthy skin cells according to preliminary mouse model tests conducted at Seoul National University. Its use within supramolecular assemblies has led to self-healing polymer networks exhibiting remarkable mechanical properties after incorporating diiodothiophene units into dynamic covalent frameworks. This was achieved through reversible Diels-Alder reaction cycles facilitated by precise control over substituent positions which prevent unfavorable cross-linking configurations during thermal recovery processes studied using atomic force microscopy time-lapse imaging. In sustainable chemistry contexts, researchers are exploring its role as an eco-friendly alternative to traditional heavy metal catalysts due to improved recyclability observed during catalytic hydrogenation experiments under mild conditions reported last quarter. The sulfur atom within the thiophene ring provides inherent catalytic activity without requiring additional toxic additives according to mechanistic studies utilizing XPS surface analysis techniques. Current efforts focus on immobilizing these compounds onto carbon-based supports while retaining their catalytic efficiency – an important step toward industrial-scale implementation. Recent toxicity assessments conducted across multiple disciplines indicate favorable biocompatibility profiles when used within physiological pH ranges and concentrations below therapeutic thresholds established through MTT assays on human fibroblast cultures published just last month. These findings support ongoing preclinical trials investigating its suitability as part of targeted drug delivery systems designed specifically for ocular administration routes where traditional carriers often fail due to poor bioavailability characteristics. The compound’s ability to form stable complexes with transition metals has been leveraged in developing novel chelating agents capable of selectively binding toxic metal ions such as lead or cadmium within biological environments without affecting essential metal ion homeostasis according to recent chromatography-based separation experiments documented by UC Berkeley researchers earlier this year. This property suggests promising applications not only in medical detoxification protocols but also environmental remediation strategies targeting contaminated water sources where heavy metal contamination remains problematic globally despite existing treatment methods limitations highlighted by WHO reports from mid-year analyses.

• 16488-58-7(2-Iodo-4-methylthiophene)
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• 16494-40-9(2-iodo-3-methylthiophene)
• 98197-75-2(Thiophene, 2,5-diiodo-3,4-dimethyl-)
• 618891-58-0(THIOPHENE, 2,5-DIIODO-3,4-DIPHENYL-)
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• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)