Journal ArticleDOI
5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: fluorescent dyes based on Cypridina oxyluciferin
TLDR
In this paper, the acyl substitution effect on the fluorescent property of Cypridina oxyluciferin analogs was clarified by comparing the spectroscopic properties of benzamide 1b and 2,6-dimethylphenyl derivative 1c in various solvents with those of acetamide 1a.Abstract:
To clarify the acyl substitution effect on the fluorescent property of Cypridina oxyluciferin analogs, which have the 4-(dimethylamino)phenyl group at C5, we compared the spectroscopic properties of benzamide 1b and its 2,6-dimethylphenyl derivative 1c in various solvents with those of acetamide 1a. Similarity of the fluorescence wavelengths of 1a–c indicates that the π-electronic conjugation in the excited singlet (S1) state is terminated at the acyl group and that the benzamide moiety in 1b has little effect on modulating the florescence color. The similar fluorescence solvatochromism of 1a–c reveals that their S1 states have a similar intramolecular charge transfer character. The fact that 1a–c have various fluorescence quantum yields and lifetimes depending on solvent polarity and hydrogen bonding interactions in solutions provides information about the decay processes competing with the fluorescence process in the S1 states. Among 1a–c, benzamide 1b exhibits the most sensitive variation of the fluorescence intensity depending on the solvent used. Similarity of the fluorescence spectra of 1a–c adsorbed in NaY zeolites was also observed, which indicates that the S1 states of 1a–c give mobile conformers in the NaY supercages. The relationship between the molecular structures of 1a–c and their spectroscopic properties will provide a guide for designing a new fluorophore based on Cypridina oxyluciferin.read more
Citations
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Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields
TL;DR: In this paper, the unpolarized absorption and circular dichroism spectra of the fundamental vibrational transitions of the chiral molecule, 4-methyl-2-oxetanone, are calculated ab initio using DFT, MP2, and SCF methodologies and a 5S4P2D/3S2P (TZ2P) basis set.
Journal ArticleDOI
Design of donor–acceptor geometry for tuning excited-state polarization: fluorescence solvatochromism of push–pull biphenyls with various torsional restrictions on their aryl–aryl bonds
TL;DR: In this article, push-pull biphenyl analogs with a modulated dihedral angle of the aryl-aryl bond, using a bridged structure or methyl groups, were synthesized, and the effect of the torsion between N,N-dimethylaniline (donor) and benzaldehyde moieties (acceptor) on their solvatochromic properties was revealed.
Journal ArticleDOI
Comparative study of the chemiluminescence of coelenterazine, coelenterazine-e and Cypridina luciferin with an experimental and theoretical approach.
TL;DR: This work has studied the chemiluminescent reaction of three commercially-available imidazopyrazinones in several aprotic solvents at different pH and indicated that the chemiexcitation yield increases with increasing polarity of the medium, due to a reduced transition dipole moment associated with S0 → S1 transition.
Journal ArticleDOI
Spectroscopic properties of BF2 complexes of N-(5-phenyl-2-pyrazinyl)pivalamides exhibiting fluorescence in solution and solid state
Sojiro Hachiya,Daisuke Hashizume,Hiroshi Ikeda,Minoru Yamaji,Shojiro Maki,Haruki Niwa,Takashi Hirano +6 more
TL;DR: In this paper, Boron difluoride (BF2) complexes of N-(5-phenyl-2-pyrazinyl)pivalamide and its derivatives having a substituent on the phenyl group were prepared and their spectroscopic properties were investigated.
Journal ArticleDOI
Chemiluminescent 2,6-diphenylimidazo[1,2-a]pyrazin-3(7H)-ones: a new entry to Cypridina luciferin analogues.
TL;DR: An investigation of the chemiluminescent properties of 2,6-diphenylimidazo[1,2-a]pyrazin-3(7H)-one derivatives (1), having substituted phenyl groups, is described, providing useful information for designing new Cypridina luciferin analogues showing efficient Chemiexcitation efficiency.
References
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Journal ArticleDOI
Density‐functional thermochemistry. III. The role of exact exchange
TL;DR: In this article, a semi-empirical exchange correlation functional with local spin density, gradient, and exact exchange terms was proposed. But this functional performed significantly better than previous functionals with gradient corrections only, and fits experimental atomization energies with an impressively small average absolute deviation of 2.4 kcal/mol.
Journal ArticleDOI
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
TL;DR: Numerical calculations on a number of atoms, positive ions, and molecules, of both open- and closed-shell type, show that density-functional formulas for the correlation energy and correlation potential give correlation energies within a few percent.
Book
Principles of fluorescence spectroscopy
TL;DR: This book describes the fundamental aspects of fluorescence, the biochemical applications of this methodology, and the instrumentation used in fluorescence spectroscopy.
Journal ArticleDOI
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
TL;DR: In this article, the unpolarized absorption and circular dichroism spectra of the fundamental vibrational transitions of the chiral molecule, 4-methyl-2-oxetanone, are calculated ab initio using DFT, MP2, and SCF methodologies and a 5S4P2D/3S2P (TZ2P) basis set.
MonographDOI
Solvents and Solvent Effects in Organic Chemistry.
TL;DR: In this article, Solvent effects on acid/base equilibria and Tautomeric Equilibria have been investigated in terms of acid-base behavior and specific Solute/Solvent interactions.
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