Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1(3H)-ones

Prlainović, Nevena Ž.; Rančić, Milica; Stoiljković, Ivana; Nikolić, Jasmina B.; Drmanić, Saša Ž.; Ajaj, Ismail; Marinković, Aleksandar D.

doi:10.2298/jsc170408003p

Cited by 7 publications

(6 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The effect may relate to the separation of charges in the D-π-A dye molecule and creation of a dipolar structure differently oriented in space as observed in other compounds with a donor−acceptor substituent displaying a low or moderate effect. 38 According to the computational calculation, the chargetransfer (CT) excitation for both conformers (E and Z) corresponds basically to the HOMO → LUMO transition (Figure 5). HOMO electrons are delocalized on the entire surface of the compound, while the LUMO is mostly on the πelectron bridge.…”

Section: ■ Introductionsupporting

confidence: 60%

A Modified Oxazolone Dye Dedicated to Spectroscopy and Optoelectronics

et al. 2022

View full text Add to dashboard Cite

Here we present a newly synthesized bifunctional organic chromophore with appealing spectroscopic and nonlinear optical features. The positions of absorption and emission maxima of the dye vary with increasing solvent polarity and exhibit positive solvatochromism. The determined change in the dipole moment upon excitation based on the Bilot and Kawski theory is 5.94 D, which corresponds to the intermolecular displacement of a charge equal to 1.24 Å. An investigated organic-based system represents a significant, repeatable, and stable over time optical signal modulation in the manner of the refractive index value. Its magnitude is varied both by optical pumping intensity as well as by external frequency modulation, which indicates that such system is an alluring and alternative core unit for optoelectronic devices and complex networks. Then, the same active system, due to the nonresonant mechanism of higher harmonics of light inducement, can provide second and third harmonic signals. According to the introduced laser line spatial modifications (parallel or perpendicular polarization directions), it is resulted in output SHG signal with magnitude varied about 100%. Its magnitude is noticeably small; however, to construct sensitive optical sensors or infrared indicators, such feature may guarantee satisfying circumstances.

show abstract

Section: ■ Introductionsupporting

confidence: 60%

A Modified Oxazolone Dye Dedicated to Spectroscopy and Optoelectronics

et al. 2022

View full text Add to dashboard Cite

show abstract

“…A high contribution of the solvent dipolar effect may result from a balanced contribution of the two opposing effects, that is, two aryl moieties constituting π-electronic entities and an oxazolone ring acting as an electron-accepting group, that cause a separation of charges by the creation of dipolar structures oriented differently in space. Such behavior was observed in compounds with a substituent displaying a low or moderate effect …”

Section: Results and Discussionmentioning

confidence: 99%

“…Such behavior was observed in compounds with a substituent displaying a low or moderate effect. 95 Negative values of the coefficients a, c, and d indicate a decrease in the shift between absorption and fluorescence spectra with an increasing polarizability SP, acidity SA, and basicity SB, while the increase of the Stokes shift of the dye in the Catalań solvent scale results in solvent dipolarity (positive value for b coefficient). Following the experimental data, the changes in the Stokes shifts with solvent type are rather small, that is, they vary from 4200 cm −1 in MCH to 5261 cm −1 in MeCN and 5107 cm −1 in MeOH.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Multifunctional Oxazolone Derivative as an Optical Amplifier, Generator, and Modulator

et al. 2022

View full text Add to dashboard Cite

An optical control of many working optoelectronic systems (real-time sensors, optical modulators, light amplifiers, or phase retarders) giving efficient optical gain or remote signal modulation is currently included as scientifically and industrially interesting. In here, an oxazolone derivative as the multifunctional organic system is given in this contribution. The molecule possesses a stilbene group and an oxazolone heteroatomic ring, which implies effective refractive index manipulation and multimode lasing action, respectively. The light modulation is repeatable and stable, also in the hundreds of Hz regime. On the other hand, the amplified optical signal can be easily generated by an external optical pumping source. Thus, signal control is fully available, as is read-in and read-out of the information in real time. Furthermore, this third-order, nonlinear, optical phenomenon using a third harmonic generation technique was also observed. We discovered that only by changing the energy and time regime of the supplied optical signal is the optical or nonlinear optical response observed. Two heteroenergetic molecular states ( trans ( E ) and cis ( Z )) can efficiently operate in modern multifunctional optoelectronic systems, which can provide and generate an optical signal. Such functionalities are commonly used in all-optical photonic switchers and logic gates and can be utilized in optical-core networks and computers.

show abstract

“…Over the past decades, the organic field effect transistor (OFET) has attracted more and more attentions due to its advantages such as low cost, easy to fabricate on a large scale. [1][2][3][4] The charge mobility of the OFET made from some small molecules by the vacuum deposition and solution processing method had already approached that of the polycrystal silicon field effect transistor whose charge mobility is over 10 cm 2 V -1 S -1 . These OFETs are considered to have promising applications in radio frequency identification device, organic lightemitting display, sensor-based equipment.…”

Section: Introductionmentioning

confidence: 99%

Study on charge mobility of hexathiapentacene and its selenium analogs

Zhou

Xia

Meng

et al. 2021

JSCS

View full text Add to dashboard Cite

The relationship between molecular geometries, crystal structures and charge mobilities of hexathiapentacene (HTP) and its three derivatives (2Se-HTP, 4Se-HTP, 6Se-HTP) were studied with density functional theory combined with hopping mechanism in the molecular and crystal level. The effect of Se substitution on the charge mobility was discussed. The calculated results showed that the derivatives exhibit good planarity and the molecular geometries have little variation during the charge transfer process. The electron mobility is 1.20 cm2 V?1 S?1 for HTP and 2.30 cm2 V?1 S?1 for 6Se-HTP, which are much larger than the corresponding hole ones, indicating that HTP and 6Se-HTP are good candidates for n-type organic semiconductor. However, 2Se-HTP and 4Se-HTP have comparable hole and electron mobilities and are suitable for ambipolar semiconductor.

show abstract

Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1(3H)-ones

Cited by 7 publications

References 14 publications

A Modified Oxazolone Dye Dedicated to Spectroscopy and Optoelectronics

A Modified Oxazolone Dye Dedicated to Spectroscopy and Optoelectronics

Multifunctional Oxazolone Derivative as an Optical Amplifier, Generator, and Modulator

Study on charge mobility of hexathiapentacene and its selenium analogs

Contact Info

Product

Resources

About