58464-25-8

Usage

Uses

Used in Organic Chemistry:
1,2,3,3-Tetramethylbenz[e]indolium iodide is used as a catalyst in organic chemistry for facilitating various chemical reactions, enhancing the efficiency and selectivity of the processes involved.
Used in Synthesis of Organic Compounds:
1,2,3,3-Tetramethylbenz[e]indolium iodide is utilized as a key intermediate in the synthesis of a range of organic compounds, contributing to the development of new materials and pharmaceuticals.
Used in Biological Research as a Fluorescent Probe:
1,2,3,3-Tetramethylbenz[e]indolium iodide is employed as a fluorescent probe for the detection and analysis of proteins and nucleic acids in biological samples, aiding in the study of molecular interactions and biological processes.
Used in Detection of Proteins and Nucleic Acids:
In the field of molecular biology, 1,2,3,3-Tetramethylbenz[e]indolium iodide serves the purpose of detecting specific proteins and nucleic acids, providing insights into their functions and interactions within complex biological systems.

InChI:InChI=1/C16H18N/c1-11-16(2,3)15-13-8-6-5-7-12(13)9-10-14(15)17(11)4/h5-10H,1-4H3/q+1

Upstream product

• 41532-84-7 2,3,3-trimethylbenzo[e]indole 
• 74-88-4 methyl iodide 
• 2243-58-5 2-naphthylhydrazine hydrochloride 
• 563-80-4 3-methyl-butan-2-one 
• 74470-85-2 2,3,3-trimethyl-3H-benzo[g]indole 
• 2243-57-4 2-hydrazinonaphthalene 

Downstream Products

• 344928-74-1 1,3,3-trimethyl-2-methylene-2,3-dihydro-1H-benzo[e]indole 
• 374694-41-4 C₂₇H₃₁N₂⁽¹⁺⁾*I^(1-) 
• 1144107-84-5 C₂₉H₂₉N₂O⁽¹⁺⁾*I^(1-) 
• 1620891-00-0 1,3,3-trimethyl-1',2'-diphenylspiro[benzo[e]indoline-2,7'-furo[3,2-f]chromene] 
• 1528736-18-6 1,1,3-trimethyl-2-((1E,3E,5E)-5-(1,1,3-trimethyl-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dien-1-yl)-1H-benzo[e]indol-3-ium iodide 
• 16111-06-1 1',3',3'-trimethyl-4',5'-benzo-6-nitrospirobenzopyran> 
• 922799-67-5 1,1,3-trimethyl-2-[(E)-2-(phenylamino)ethenyl]-1H-benzo[e]indol-3-ium iodide 
• 1144107-80-1 C₄₀H₄₂N₂O₂ 

Relevant academic research and scientific papers

Viscosity sensitive semisquaraines based on 1, 1, 2-trimethyl-1H-benzo[e]indole: Photophysical properties, intramolecular charge transfer, solvatochromism, electrochemical and DFT study

1, 1, 2-Trimethyl-1H-benzo[e]indole based D-π-A type semisquaraines denoted as, SSK 1–3 were synthesized to investigate their primary photophysical properties, intramolecular charge transfer, solvatochromism, electrochemical properties and viscosity dependent enhanced emission. These semisquaraines contain 1, 1, 2-trimethyl-1H-benzo[e]indole and squaryl ring as donor and acceptor respectively. These dyes displayed absorption between 437 and 444 nm and emission in the range of 469–493 nm. Stokes shift of the synthesized compounds were in the range of 32–54 nm. The SSK 1–3 exhibited intense yellow-orange colored solid state fluorescence (Fmax = 520–549 nm). These dyes exhibited intramolecular charge transfer characteristics which were confirmed from their oscillator strengths, transition dipole moments, ground and excited state dipole moments and generalized Mulliken-Hash analysis (GMH). Moreover, the positive emission solvatochromic behaviour (Δλem = 21–24 nm) of these dyes was quantitatively analyzed from different solvent polarity plots. More interestingly, these D-π-A type FMRs displayed viscosity sensitive emission enhancement (23 to 32 fold increase in fluorescence intensity) in 99% methanol:glycerol system at the visible region of electromagnetic spectrum (450–650 nm). The molecular structures of SSK 1–3 were correlated with photophysical properties using density functional theory (DFT) and theoretical absorption spectra in eight different solvents were obtained from time dependent density functional theory (TD-DFT).

A fluorescent turn-on probe based on benzo [E] indolium for cyanide ion in water with high selectivity

A highly selective fluorescent turn-on probe for CN- bearing a benzo [e] indolium group as a fluorophore and binding site was reported. The detection of CN- was performed via the nucleophilic attack of CN - toward the benzo [e] indolium group of the probe, resulting in a prominent fluorescence enhancement and an obvious color change. The probe shown a highly selectivity in water and could be performed in a range of pH value between 6 and 9. The detection limit was 4.6 × 10-8 M, which could be detected CN- in drinking water. A simple paper test strip system for the rapid monitoring of CN- was developed.

A novel off-on fluorescent probe for sensitive imaging of mitochondria-specific nitroreductase activity in living tumor cells

Sensitive and selective detection and imaging of nitroreductase (NTR) in cancer cells is of great importance for better understanding their biological functions. Since there are a few fluorescent probes concerning NTR activity specifically located in mito

A novel endoplasmic reticulum-targeted ratiometric fluorescent probe based on FRET for the detection of SO2 derivatives

A novel FRET-based fluorescence probe, NBIS, constructed by benzoindole-based hemicyanine as an acceptor and naphthalimide derivatives as a donor was developed for the detecting of sulfur dioxide (SO2) derivatives. Probe NBIS exhibited high energy transfer efficiency (89%) and showed high sensitivity (LOD: 16.2 nM) toward HSO3?/SO32?. Probe NBIS could target the endoplasmic reticulum (ER) and was applied to image exogenous and endogenous HSO3?/SO32? in living cells.

Large-sized benzo[: E] indolium salt single crystals with high optical nonlinearity

In this paper, a series of D-π-A type benzo[e]indolium salts with highly efficient nonlinear optical performance has been synthesized. Out of the three new benzo[e]indolium salts, (E)-2-(2-hydroxy-3-methoxystyryl)-1,1,3-trimethyl-1H-benzo[e]indol-3-ium iodide (HMTB-1) and (E)-2-(2-hydroxy-4-methoxystyryl)-1,1,3-trimethyl-1H-benzo[e]indol-3-ium iodide (HMTB-2) possess SHG properties, and their maximum powder second harmonic generation (SHG) efficiency is around 0.6 times that of DAST (4-N,N-dimethylamino-4′-N′-methyl-stilbazolium tosylate) at a non-resonant wavelength of λ = 1570 nm. Single crystals of the two noncentrosymmetric salts were successfully grown by using a slow cooling method, and we were able to obtain very large bulk single crystals, about 17 mm × 9 mm × 3 mm, of HMTB-2. X-ray crystallographic analysis indicated that both of the new salts belong to the monoclinic space group Cc (point group m, Z = 4). HMTB-1 forms a noncentrosymmetric phase with methanol through hydrogen bonding.

A cancer cell-specific benzoxadiazole-based fluorescent probe for hydrogen sulfide detection in mitochondria

The present work describes the design and biological applications of a novel colorimetric and fluorescence turn-on probe for hydrosulfide detection. The probe was designed to introduce hemicyanine as the fluorescent skeleton and 7-nitro-1,2,3-benzoxadiazole as the recognition site. The optical properties and responses of the probe towards HS-, anions and some biothiols indicate an impressively high selectivity of the probe towards HS- such that it can be effectively used as an indicator for monitoring the level of HS- in living cells. In biological experiments using the probe, the H2S levels are found to be higher in cancer cells than in normal cells. In addition, the probe is shown to specifically and rapidly detect endogenous H2S, which is produced primarily in the mitochondria of cancer cells, as demonstrated by a co-localization experiment using specific trackers for the detection of cellular organelles in pharmacological inhibition or stimulation studies, without any significant cytotoxic effects. Thus, the results of the chemical and biological experiments described herein demonstrate the potential of this novel probe to specifically, safely, and rapidly detect H2S to distinguish cancer cells from normal cells by targeting it specifically in mitochondria. This journal is

FRET-based ratiometric fluorescent detection of arginine in mitochondrion with a hybrid nanoprobe

A ratiometric fluorescent hybrid nanoprobe CDs-1 for arginine (Arg), exhibiting high sensitivity (the limit of detection, LOD, being 6.5 × 10?8 mol/L) and excellent selectivity and anti-interference ability, was fabricated through fluorescence resonance energy transfer (FRET) and the electrostatic attraction between positively-charged hemicyanine molecules and negatively-charged carbon dots (CDs). Arg can be quantitatively detected in the concentration range from 6.0 × 10?5 mol/L to 2.7 × 10?4 mol/L. Further, due to its ability to target mitochondrion and low cytotoxicity, intracellular Arg was successfully tracked through ratiometric fluorescence imaging.

Ratiometric fluorimetric and colorimetric probe for sensing and imaging pH changes in living cells

Cell, enzyme, and tissue activity in living organisms are closely related to intracellular pH. Detecting the changes of intracellular pH is important to understanding the physiological and pathological changes in the process of crucial cell metabolism. A pH probe (HTBI) based on hemicyanine was synthesized. The probe solution displayed a marked colour change from yellow to amaranth with the pH increase from neutral to basic; simultaneously, the emission spectra showed a significant red shift. The probe exhibited a ratiometric fluorescence emission (F586nm/F542nm) characteristic of pKa 8.82. As expected, HTBI exhibited high sensitivity and selectivity for pH, fine photostability, reversibility, and low cytotoxicity. Therefore, it would be a very useful tool for measuring the intracellular pH changes.

Bioorthogonal Ligation-Activated Fluorogenic FRET Dyads

An energy transfer-based signal amplification relay concept enabling transmission of bioorthogonally activatable fluorogenicity of blue-excitable coumarins to yellow/red emitting cyanine frames is presented. Such relay mechanism resulted in improved cyani

Towards new NIR dyes for free radical photopolymerization processes

The use of cheap and safe near-infrared (NIR) light is still the subject of intense research efforts but remains a huge challenge due to the associated low photon energy (wavelength from 0.78 to 2.5 μm). In this study, a series of 17 NIR dyes mainly based on a well-established cyanine scaffold is proposed. Remarkably, 11 of them were never synthesized before. Markedly, noncharged structures, negatively charged cyanine bearing Na+ as counter cation, and positively charged cyanines bearing (B(Ph)4?) or (I?) as counter anions were examined as promising NIR light photoinitiating systems. Excellent photoinitiating abilities were found for some reported dyes when used in combination with iodonium salt and amine. Markedly, photothermal effects with a huge heater behavior were also observed for different NIR dye structures. Interestingly, the synthesis of interpenetrating polymer networks (IPNs, e.g., for the polymerization of acrylate/epoxy monomer blends) can also be carried out upon NIR light with the proposed systems.