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Emission color-tunable oxazol(in)yl-substituted excited-state intramolecular proton transfer (ESIPT)-based luminophores.

ABSTRACT: Oxazolinyl- and arylchalcogenazolyl-substituted hydroxyfluorenes exhibiting excited-state intramolecular proton transfer (ESIPT) are described as potent and highly modular luminophores. Emission color tuning was achieved by varying the π-expansion and the insertion of different chalcogen atoms.

SUBMITTER: Gobel D

PROVIDER: S-EPMC8517962 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Tuning excited-state-intramolecular-proton-transfer (ESIPT) process and emission by cocrystal formation: a combined experimental and theoretical study.

Project description:The formation of two-component molecular cocrystals can lead to the tunable excited state intramolecular proton transfer (ESIPT) process and emission, as first confirmed by both experimental and computational studies.

| S-EPMC5399640 | biostudies-literature

Near infrared two-photon-excited and -emissive dyes based on a strapped excited-state intramolecular proton-transfer (ESIPT) scaffold.

Project description:Fluorophores that can undergo excited-state intramolecular proton transfer (ESIPT) represent promising scaffolds for the design of compounds that show red-shifted fluorescence. Herein, we disclose new near infrared-emissive materials based on a dialkylamine-strapped 2,5-dithienylpyrrole as an ESIPT scaffold. The introduction of electron-accepting units to the terminal positions of this scaffold generates acceptor-?-donor-?-acceptor (A-?-D-?-A) type ?-conjugated compounds. Following the ESIPT, the electron-donating ability of the core scaffold increases, which results in a substantially red-shifted emission in the NIR region, while increasing the oscillator strength. The electron-accepting units play a vital role to achieve intense and red-shifted emission from the ESIPT state. The strapped dialkylamine chain that forms an intramolecular hydrogen bond is also essential to induce the ESIPT. Moreover, an extended A-?-D-?-A skeleton enables two-photon excitation with the NIR light. One of the derivatives that satisfy these features, i.e., borylethenyl-substituted 5, exhibited an intense NIR emission in polar solvents such as acetone (?em = 708 nm, ?F = 0.55) with a strong two-photon-absorption band in the NIR region.

| S-EPMC5897875 | biostudies-other

Theoretical insights into excited-state hydrogen bonding effects and intramolecular proton transfer (ESIPT) mechanism for BTS system.

Project description:In this work, N,N'-bis(salicylidene)-(2-(3',4'-diaminophenyl)benzothiazole) (named as "BTS") system was studied about its excited-state intramolecular proton transfer (ESIPT) process. The analyses about reduced density gradient (RDG) reveal the formation of two intramolecular hydrogen bonds in BTS system. Bond lengths and angles, infrared (IR) vibrations as well as frontier molecular orbitals (MOs) using TDDFT method indicate that the strength of hydrogen bond should be enhanced in the S1 state. Particularly, hydrogen bond O1-H2···N3 undergoes larger variations compared with O4-H5···N6, which infers that hydrogen bond O1-H2···N3 may play a decisive role in the ESIPT process of BTS system. Given the two hydrogen bonds of BTS molecule, two types of potential energy curves have been constructed, which confirms that only single proton transfer process occurs due to lower energy barrier along with O1-H2···N3 rather than O4-H5···N6. This work not only presents a reasonable explanation for previous experiment, but also clarifies the specific ESIPT mechanism for BTS system.

| S-EPMC7083891 | biostudies-literature

Donor-acceptor substituted phenylethynyltriphenylenes - excited state intramolecular charge transfer, solvatochromic absorption and fluorescence emission.

Project description:Several 2-(phenylethynyl)triphenylene derivatives bearing electron donor and acceptor substituents on the phenyl rings have been synthesized. The absorption and fluorescence emission properties of these molecules have been studied in solvents of different polarity. For a given derivative, solvent polarity had minimal effect on the absorption maxima. However, for a given solvent the absorption maxima red shifted with increasing conjugation of the substituent. The fluorescence emission of these derivatives was very sensitive to solvent polarity. In the presence of strongly electron withdrawing (-CN) and strongly electron donating (-NMe₂) substituents large Stokes shifts (up to 130 nm, 7828 cm⁻¹) were observed in DMSO. In the presence of carbonyl substituents (-COMe and -COPh), the largest Stokes shift (140 nm, 8163 cm⁻¹) was observed in ethanol. Linear correlation was observed for the Stokes shifts in a Lippert-Mataga plot. Linear correlation of Stokes shift was also observed with E(T)(30) scale for protic and aprotic solvents but with different slopes. These results indicate that the fluorescence emission arises from excited state intramolecular charge transfer in these molecules where the triphenylene chromophore acts either as a donor or as an acceptor depending upon the nature of the substituent on the phenyl ring. HOMO-LUMO energy gaps have been estimated from the electrochemical and spectral data for these derivatives. The HOMO and LUMO surfaces were obtained from DFT calculations.

| S-EPMC2981938 | biostudies-literature

Natural Born Laser Dyes: Excited-State Intramolecular Proton Transfer (ESIPT) Emitters and Their Use in Random Lasing Studies.

Project description:A series of five excited-state intramolecular proton transfer (ESIPT) emitters based on a 2-(2'-hydroxyphenyl) benzoxazole (HBO) scaffold, functionalized with a mono-or bis-(trialkylsilyl) acetylene extended spacer are presented. Investigation of their photophysical properties in solution and in the solid-state in different matrix, along with ab initio calculations gave useful insights into their optical behavior. Random lasing studies were conducted on a series of PMMA doped thin films, showing the presence of stimulated emission above the threshold of pumping energy density (ρth ≈ 0.5-2.6 mJ cm-2). In this work, the similarity of four level laser systems is discussed in light of the ESIPT photocycle.

| S-EPMC6723810 | biostudies-other

Combined TDDFT and AIM Insights into Photoinduced Excited State Intramolecular Proton Transfer (ESIPT) Mechanism in Hydroxyl- and Amino-Anthraquinone Solution.

Project description:Time-dependent density functional theory (TDDFT) and atoms in molecules (AIM) theory are combined to study the photoinduced excited state intramolecular proton transfer (ESIPT) dynamics for eight anthraquinones (AQs) derivatives in solution. The calculated absorption and emission spectra are consistent with the available experimental data, verifying the suitability of the theory selected. The systems with the excited-state exothermic proton transfer, such as 1-HAQ, 1,5-DHAQ and TFAQ, emit completely from transfer structure (T), while the reactions for those without ESIPT including 1,4-DHAQ and AAAQ appear to be endothermic. Three reaction properties of three systems (1,8-DHAQ, DCAQ and CAAQ) are between the exothermic and endothermic, sensitive to the solvent. Energy scanning shows that 1,4-DHAQ and AAAQ exhibit the higher ESIPT energy barriers compared to 1-HAQ, 1,5-DHAQ and TFAQ with the "barrierless" ESIPT process. The ESIPT process is facilitated by the strengthening of hydrogen bonds in excited state. With AIM theory, it is observed that the change in electrons density ρ(r) and potential energy density V(r) at BCP position between ground state and excited state are crucial factors to quantitatively elucidate the ESIPT.

| S-EPMC5653788 | biostudies-literature

Red-Shift (2-Hydroxyphenyl)-Benzothiazole Emission by Mimicking the Excited-State Intramolecular Proton Transfer Effect.

Project description:Novel strategies to optimize the photophysical properties of organic fluorophores are of great significance to the design of imaging probes to interrogate biology. While the 2-(2-hydroxyphenyl)-benzothiazole (HBT) fluorophore has attracted considerable attention in the field of fluorescence imaging, its short emission in the blue region and low quantum yield restrict its wide application. Herein, by mimicking the excited-state intramolecular proton transfer (ESIPT) effect, we designed a series of 2-(2-hydroxyphenyl)-benzothiazole (HBT) derivatives by complexing the heteroatoms therein with a boron atom to enhance the chance of the tautomerized keto-like resonance form. This strategy significantly red-shifted the emission wavelengths of HBT, greatly enhanced its quantum yields, and caused little effect on molecular size. Typically, compounds 12B and 13B were observed to emit in the near-infrared region, making them among the smallest organic structures with emission above 650 nm.

| S-EPMC8738082 | biostudies-literature

Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases.

Project description:Excited state dynamics of common yellow dye quinophthalone (QPH) was probed by femtosecond transient absorption spectroscopy. Multi-exponential decay of the excited state and significant change of rate constants upon deuterium substitution indicate that uncommon nitrogen-to-oxygen excited state intramolecular proton transfer (ESIPT) occurs. By performing density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations, we found that adiabatic surface crossing between the S1 and S2 states takes place in the photoreaction. Unlike most cases of ESIPT, QPH does not exhibit tautomer emission, possibly due to internal conversion or back-proton transfer. The ESIPT of QPH presents a highly interesting case also because the moieties participating in ESIPT, quinoline and aromatic carbonyl, are both traditionally considered as photobases.

| S-EPMC5478638 | biostudies-literature

Intramolecular electron-induced proton transfer and its correlation with excited-state intramolecular proton transfer.

Project description:Electron-induced proton transfer depicts the proton motion coupled with the attachment of a low-energy electron to a molecule, which helps to understand copious fundamental chemical processes. Intramolecular electron-induced proton transfer is a similar process that occurs within a single molecule. To date, there is only one known intramolecular example, to the best of our knowledge. By studying the 10-hydroxybenzo[h]quinoline and 8-hydroxyquinoline molecules using anion photoelectron spectroscopy and density functional theory, and by theoretical screening of six other molecules, here we show the intramolecular electron-induced proton transfer capability of a long list of molecules that meanwhile have the excited-state intramolecular proton transfer property. Careful examination of the intrinsic electronic signatures of these molecules reveals that these two distinct processes should occur to the same category of molecules. Intramolecular electron-induced proton transfer could have potential applications such as molecular devices that are responsive to electrons or current.

| S-EPMC6414547 | biostudies-literature

Excited-state intramolecular proton-transfer reaction demonstrating anti-Kasha behavior.

Project description:We report unusual photophysical properties observed on two newly designed 3-hydroxychromone derivatives exhibiting the excited-state intramolecular proton transfer (ESIPT) reaction. The efficiency of ESIPT reaction is greatly enhanced upon excitation with high energy quanta to S n (n > 1) levels in low-polarity solvents. Based on detailed analyses of excitation and emission spectra as well as time-resolved emission kinetics we derive that conditions, in which this phenomenon contradicting Kasha's rule is observed, are quite different from that for observation of anti-Kasha emission.

| S-EPMC5952995 | biostudies-literature

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