7-Diethylamino-3-thenoylcoumarin

• CAS: 77820-11-2
• Catalog Number: ACM77820112
• Category: Main Products
• Molecular Weight: 327.4
• Molecular Formula: C18H17NO3S

Case Study

Effect of solvents on the absorption and fluorescence spectra of 7-diethylamino-3-thenoylcoumarin

Basavaraja, Jana, S. R. Inamdar, and HM Suresh Kumar. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 137 (2015): 527-534.

The effect of solvents of different polarities on the absorption and fluorescence spectra and dipole moment of laser dyes: 7-diethylamino-3-thenoylcoumarin (DETC) has been studied. The band shifts in the absorption spectrum are small compared to the emission spectrum. The spectral shifts were correlated with Catalan parameters using a linear solvation energy relationship. It revealed that the absorption is more strongly influenced by nonspecific interactions measured by solvent polarity and in case of fluorescence the solvent dipole contribution is significant. The deep color shifts observed in the absorption and emission spectra with increasing solvent polarity imply that the transitions involved are p p. The solvatochromic correlations were used to estimate the excited state dipole moment using the experimentally determined ground state dipole moment.
The laser dye 7-diethylamino-3-thenoylcoumarin (DETC) was used without further purification. All solvents used were of HPLC grade, transparent and non-fluorescent in the excitation and fluorescence emission ranges. The absorption spectra were recorded using an absorption spectrophotometer and the fluorescence spectra were recorded using a fluorescence spectrophotometer. All measurements were performed at room temperature, keeping the dye concentration very low to avoid self-absorption. The ground state dipole moment of DETC was also calculated using the Guggenheim method. Dilute solutions of approximately 10^M prepared in toluene solvent were used for the studies.

7-Diethylamino-3-thenoylcoumarin for lithography studies

Wollhofen, Richard, et al. Optics express 21.9 (2013): 10831-10840.

Two-photon direct laser writing (DLW) lithography is limited in terms of achievable structure size and structure resolution. Adding stimulated emission depletion (STED) to DLW can overcome both limitations. Using visible light for two-photon DLW (780 nm) and STED (532 nm), lateral structure sizes of 55 nm were obtained, around the sparrow limit of 100 nm, presenting two sharply separated lines with a spacing of only 120 nm. The photoresist used in these experiments was a mixture of tri- and tetraacrylates with 7-diethylamino-3-thenoylcoumarin as a photoinitiator that can be easily quenched by STED.
The composition of the photoresist was a 40:60 mixture (by weight) of pentaerythritol tetraacrylate (PETTA) and pentaerythritol triacrylate (PETA), including 300-400 ppm of monomethyl ether hydroquinone. 0.25 wt. % of the photosensitizer DETC (7-diethylamino-3-thenoylcoumarin) was added. The photoresist was stirred for 20 min to thoroughly mix all the components. DETC dissolved in PETA showed a single-photon absorption peak with a maximum at a wavelength of 420 nm and a fluorescence emission maximum at 480 nm that decreased to 20% at 532 nm. To initiate polymerization, DETC was excited by a 780 nm laser pulse. STED was performed by a continuous wave (CW) 532 nm laser.

7-Diethylamino-3-thenoylcoumarin for studying low-fluorescence initiators

Gvindzhiliia, Georgii, et al. ACS Applied Optical Materials 1.5 (2023): 945-951.

Stimulated emission depletion (STED) has been used to break the diffraction limit of fluorescence microscopy. Inspired by this success, similar approaches have also been used to reduce the size of structures in three-dimensional sub-diffraction optical lithography. The initiator Michaelis ethyl ketone (MEK), which has not been used in STED-inspired lithography so far, is introduced. Nanostructures written with MEK show lower autofluorescence in the visible range compared to the commonly used 7-diethylamino-3-thenoylcoumarin (DETC). MEK is therefore promising for use as an initiator for proteins or cell scaffolds in physiological studies, since the autofluorescence of DETC has so far excluded the use of the green emission channel in multicolor fluorescence or confocal microscopy.
The two acrylates were combined with each other at 0.25 wt % of one of the two initiators, resulting in four possible resin blends: (PETA/DETC), (DPPHA:DDA/DETC), (PETA/MEK), and (DPPHA:DDA/MEK). The first combination (PETA/7-diethylamino-3-thenoylcoumarin (DETC)) is a photoresist widely used in STED-inspired sub-diffraction lithography. Scanning electron microscopy (SEM) images were obtained using SEM after evaporating about 10 nm of gold. To determine the axial dimensions of the three-dimensional structures, SEM imaging was performed after tilting the sample at 60°. Photoluminescence (PL) spectra of the polymers were obtained after forming thin films of the four composites and curing them under UV light.

7-Diethylamino-3-thenoylcoumarin for the fabrication of composites

Hu, Qin, et al. Scientific reports 7.1 (2017): 17150.

Complex three-dimensional gold-containing nanocomposite structures were fabricated by simultaneous two-photon polymerization and photoreduction. Increasing the salt afforded smaller feature sizes, down to line widths of 78 nm, and this level of structural complexity represents a significant advance in fabrication sophistication. A general method was developed to efficiently mix pentaerythritol triacrylate (PETA) with gold chloride hydrate (HAuCl4∙3H2O), where the gold salt concentration could be adjusted from 0 to 20 wt% as desired. 7-Diethylamino-3-thenoylcoumarin (DETC) was used as a photoinitiator. Only 0.5 wt% of DETC was required to promote polymerization and photoreduction of up to 20 wt% of gold salt. This efficiency is the highest ever achieved for the fabrication of gold-containing composites by two-photon lithography. Transmission electron microscopy (TEM) analysis confirmed the presence of small metal nanoparticles (major axis 5.4 ± 1.4 nm/minor axis 3.7 ± 0.9 nm) embedded in the polymer matrix, while X-ray photoelectron spectroscopy (XPS) confirmed their presence in the zero-valent oxidation state. UV-Vis spectroscopy determined that they exhibited localized surface plasmon resonance (LSPR) properties.
Due to the limited solubility of 7-diethylamino-3-thenoylcoumarin (DETC) in PETA (<2 wt%), mixtures of 0.5 wt%, 1 wt%, and 1.5 wt% DETC were investigated. In all spectra, no absorption band was observed at the laser wavelength of 780 nm, implying that the photoinduced reaction is associated with the excitation of the chemical species by a two-photon absorption process. Composite fabrication was performed by first loading a drop of the resin mixture onto a clean coverslip. The coverslip was then placed on the Nanoscribe for two-photon processing. After laser exposure, the samples were first immersed in propylene glycol monomethyl ether acetate (PGMEA) for 15 min and then immersed in 2-propanol for 2 min to remove the unreduced gold salt and residual monomer. Finally, the samples were dried with nitrogen.

Custom Q&A

What is the molecular formula of 7-Diethylamino-3-thenoylcoumarin?

The molecular formula is C18H17NO3S.

What are the synonyms for 7-Diethylamino-3-thenoylcoumarin?

The synonyms are 7-(Diethylamino)-3-(thiophene-3-carbonyl)-2H-chromen-2-one, SCHEMBL51515, AKOS027314041, and AS-70724.

How much does 7-Diethylamino-3-thenoylcoumarin weigh?

It has a molecular weight of 327.4 g/mol.

When was 7-Diethylamino-3-thenoylcoumarin created?

It was created on December 5, 2007.

When was 7-Diethylamino-3-thenoylcoumarin last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 7-Diethylamino-3-thenoylcoumarin?

The IUPAC name is 7-(diethylamino)-3-(thiophene-3-carbonyl)chromen-2-one.

What is the InChI of 7-Diethylamino-3-thenoylcoumarin?

The InChI is InChI=1S/C18H17NO3S/c1-3-19(4-2)14-6-5-12-9-15(18(21)22-16(12)10-14)17(20)13-7-8-23-11-13/h5-11H,3-4H2,1-2H3.

What is the InChIKey of 7-Diethylamino-3-thenoylcoumarin?

The InChIKey is GDRWYGWOZQAYRI-UHFFFAOYSA-N.

What is the canonical SMILES of 7-Diethylamino-3-thenoylcoumarin?

The canonical SMILES is CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C(=O)C3=CSC=C3.

What is the topological polar surface area of 7-Diethylamino-3-thenoylcoumarin?

The topological polar surface area is 74.8Ų.