Effects of different proton donor and acceptor groups on excited-state intramolecular proton transfers of amino-type and hydroxy-type hydrogen-bonding molecules: theoretical insights

Kanlayakan, Narissa; Kerdpol, Khanittha; Prommin, Chanatkran; Salaeh, Rusrina; Chansen, Warinthon; Sattayanon, Chanchai; Kungwan, Nawee

doi:10.1039/c7nj00984d

Cited by 52 publications

(20 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Electronic cloud surrounding (N―H) proton donor at the LUMO level shrinks to a larger extent in comparison to that observed at the HOMO level, and such changes were not observed for the proton acceptor moiety (C═O) . Such observed changes over electronic cloud support good interactions between proton donor and acceptor moieties heading toward a better proton translocation at the S1 …”

Section: Resultsmentioning

confidence: 81%

“…BTN possesses a dihedral angle of 39.9° at its ground state and 36.8° at its excited state between the planes connecting the bithiophene unit and the pyridine ring on both the arms. The planar structure might well support the proton transfer process in a system in comparison with a sterically hindered structure . The dihedral angle between the planes possessing N―H and ―C═O is 1.7° for BTN at S0 and increases to a value of 2.3° at S1, whereas BTO exhibits 0.0° at S0 and increases to a value of 0.8° at S1 with BTS maintaining 0.0° for both S0 and S1.…”

Section: Resultsmentioning

confidence: 94%

“…Intramolecular hydrogen bond distance denoted as R and R′ is shortened at excited state in comparison with that of ground state for all the molecules. The shortening of intramolecular hydrogen bond distance is highly suggestive of possible proton transfer via a prelinked hydrogen bond pathway . BTN shows a substantial change in the R and R′ at their excited state in comparison with that of the ground state possibly owing to the effect of six‐membered pyridine spreading its influence over the proton donor‐acceptor moiety.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Mohan

Satyanarayan

Trivedi

2019

J of Physical Organic Chem

View full text Add to dashboard Cite

Hydrazides are known to exhibit keto‐enol tautomerism upon photoexcitation. Theoretical aspects uncovering excited state intramolecular proton transfer (ESIPT) of N‐acylsubstituted hydrazides with bithiophene core have been investigated. Geometrical aspects of the system are expected to undergo double proton translocation at its excited state. However, potential energy surface study for all the molecules reveals an impossible concurrent double proton translocation and to a greater extent dubious step‐wise double proton translocation in the system. Potential energy scans reveal molecules possessing a lower forward barrier at its excited state in comparison with their ground state suggestive of possible excited state single proton transfer. Geometrical attributes and spectral analysis suggest the strengthening of intramolecular hydrogen bond (N―H▪▪▪O) at its excited state, favoring single proton translocation. Theoretical estimation of electronic energy transition for all the conformers yields good correlation with the experimental figures with an energy overestimation <0.17 eV.

show abstract

Section: Resultsmentioning

confidence: 81%

Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Mohan

Satyanarayan

Trivedi

2019

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

“…Numerous attempts have been made to design ESIPT‐based molecular units conjugated with various additional receptor sites such as 2‐(2′‐hydroxyphenyl)benzoxazole, 2‐(2′‐hydroxyphenyl)imidazole, 2‐phenyl‐3‐hydroxy‐4(1H)‐quinolone, 3‐hydroxyflavone, hydroxybenzo[ h ]quinoline, and 2‐(2′‐hydroxyphenyl)imidazo[1,2‐ a ]pyridines along with unusual naphthylphenols and phenylnaphthols for sensing and biological studies. Such units showed emission in organic/mixed aqueous media, which was triggered through the ESIPT process.…”

Section: Designing Of Probes and Its Strategic Insightsmentioning

confidence: 99%

Electronically‐tuned 2‐(2′‐Hydroxyphenyl)‐4‐pyrenylthiazole through Bond Energy Transfer Donor–Acceptor Couples: Sensing and Biological Applications

Huh

Pandith

Cho

et al. 2018

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

A novel pyrene‐conjugated 2‐(2′‐hydroxyphenyl)thiazole probe (HPTP, 1) was prepared, and its photophysical and sensing properties were investigated and compared to those of four model compounds. HPTP effectively detects CN− and glycerol in DMSO, with “turn off” at 425 nm and “turn on” at 495 nm. The sensing ability of 1 towards CN− ions in DMSO, mediated by the hydrogen bonding‐induced disaggregation of aggregates, resulted in the quenching of ESIPT emission at 425 nm. By contrast, in a DMSO–glycerol mixed medium, the aggregate size increased together with the increased degree of intermolecular π–π interactions between two pyrene units located on adjacent molecules, and resulted in partial inhibition of energy/charge transfer from the pyrene unit to the thiazole unit in the excited state. Excitation energy transfer with increased photostability of the ESIPT core was effectively demonstrated in Candida albicans cell lines.

show abstract

“…A significant increase in both the acidic and basic property of proton donor as well as the acceptor groups in the excited state leads the ESIPT process to occur in ultrafast time scale . Typical ESIPT time constants (τ ESIPT ) ranging from few tens of femtoseconds to few picoseconds are reported in the literature for different systems .…”

Section: Introductionmentioning

confidence: 99%

Excited State Decay Dynamics in 3‐Formyl‐4‐hydroxy Benzoic Acid: Understanding the Global Picture of an ESIPT‐Driven Multiple‐Emissive Species

et al. 2019

View full text Add to dashboard Cite

Relaxation dynamics of excited state intramolecular proton transfer (ESIPT) probe 3‐formyl‐4‐hydroxy benzoic acid (FHBA) was studied by steady state, nanosecond time‐resolved fluorescence (TRF) and femtosecond transient absorption (TA) experiments in combination with adequate level of quantum chemical calculations. Global analysis of the transient data with target model reveals that enol conformers of both the neutral FHBA (I) and proton dissociated mono‐anionic species (III) undergo ESIPT in picosecond time scale (τESIPT ≈1.2 ps) towards the formation of corresponding vibrationally hot keto structure. Rapid intramolecular vibrational cooling (τ≈20 ps) follows singlet deactivation of the corresponding conformers with fluorescence lifetime (τfluo) of ∼5.1 and 2.0 ns, respectively as confirmed from stimulated emission (SE) and/or time resolved fluorescence experiments. Selective excitation of the di‐anionic structure (II) at 400 nm follows relatively simple excited state non‐ESIPT decay dynamics having fluorescence emission at 500 nm with τfluo ≈ 1.2 ns. Complete optimization of individual structures and construction of ESIPT profile was done by HF(CIS) as well as (TD)DFT calculation using 6–311++G(d,p) basis set and found to be consistent with the experimental observations.

show abstract

Effects of different proton donor and acceptor groups on excited-state intramolecular proton transfers of amino-type and hydroxy-type hydrogen-bonding molecules: theoretical insights

Abstract: The effect of proton donors (NH and OH) on ESIPT was investigated using DFT and TD-DFT.

Cited by 52 publications

References 49 publications

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Electronically‐tuned 2‐(2′‐Hydroxyphenyl)‐4‐pyrenylthiazole through Bond Energy Transfer Donor–Acceptor Couples: Sensing and Biological Applications

Excited State Decay Dynamics in 3‐Formyl‐4‐hydroxy Benzoic Acid: Understanding the Global Picture of an ESIPT‐Driven Multiple‐Emissive Species

Contact Info

Product

Resources

About