Carbazole-containing push–pull chromophore with viscosity and polarity sensitive emissions: Synthesis and photophysical properties

Telore, Rahul D.; Sekar, Nagaiyan

doi:10.1016/j.dyepig.2016.02.012

Cited by 29 publications

(10 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…To the best of our knowledge, the value of x obtained for TPSI I, i.e. 1.02, is the highest value reported so far in the literature [41][42][43][44][45][46] , supporting its high sensitivity to changes in the viscous medium. The detection limit for TPSI I is 0.93cp and for TPSI PF 6 is 1.29 cP.…”

Section: Iii) Photophysical Property Studiessupporting

confidence: 56%

Engineering a light-driven cyanine based molecular rotor to enhance the sensitivity towards a viscous medium

et al. 2021

View full text Add to dashboard Cite

show abstract

Section: Iii) Photophysical Property Studiessupporting

confidence: 56%

Engineering a light-driven cyanine based molecular rotor to enhance the sensitivity towards a viscous medium

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Hence, 5 c can be considered as FMR active fluorophore due to its good sensitivity towards the viscous environment. Moreover, these fluorophores demonstrate very high emission wavelengths ( ∼ 627 nm) as compared to well‐known traditional rotor 6 (x=0.41) as well as the reported analogous fluorophore 1 . Viscosity sensitivity in the deep red region is highly essential due to its biological importance and as 5 b and 5 c emit above 600 nm due to the introduction of secondary donor group can be considered as a suitable FMRs in the deep red region.…”

Section: Resultsmentioning

confidence: 80%

“…Moreover, these fluorophores demonstrate very high emission wavelengths ( ∼ 627 nm) as compared to well-known traditional rotor 6 (x = 0.41) as well as the reported analogous fluorophore 1. [113] Viscosity sensitivity in the deep red region is highly essential due to its biological importance and as 5 b and 5 c emit above 600 nm due to the introduction of secondary donor group can be considered as a suitable FMRs in the deep red region. Table S5, it is observed that the bond lengths in 5 a-c decrease and increase alternatively thereby signifying CT characteristics.…”

Section: Sensitivity Of Emission To Viscositymentioning

confidence: 99%

N‐Ethyl Carbazole Derived D‐π‐A‐π‐D Based Fluorophores: Consolidated Spectroscopic, Viscosity and DFT Studies

2019

Self Cite

View full text Add to dashboard Cite

This article reports design and synthesis of three new fluorophores (5 a‐c) with the donor‐π‐acceptor‐π‐donor motif, where dicyano vinylene group is the central acceptor, N‐ethyl carbazole group is a fixed donor and varying the N‐substituted secondary donors so as to study their photophysical behavior. Based on the systematic photophysical and theoretical reconnaissances, the fluorophores structure‐property relationships are defined. Their spectral and photophysical behaviors are affected by the solvent polarity, with a significant bathochromic shift in emission and large Stoke shifts being observed in polar solvents. Contrary to dipolar asymmetric analogue this system shows an efficient intramolecular charge transfer as observed from various solvent polarity plots. For 5 a, 5 b, and 5 c, the viscosity induced emission studies show respectively 3.78, 6.53, and 6.82 times enhancement in their fluorescence intensity and hence act as a fluorescent molecular rotor (FMR). The structure and electronic properties of these fluorophores were evaluated using density functional theory computations using B3LYP/6‐311++G(d,p). The frontier molecular orbitals and the optimized geometry reveal that secondary donors in each fluorophore donate the electron and not the N‐ethyl carbazole group which is more twisted. The non‐linear and linear optical properties were determined employing solvatochromic and computational methods in solvents of varying polarities with results falling within the expected limiting values. The linear and non‐linear optical properties of the fluorophores change with the strength of different secondary donors used and solvent polarity. The two photon absorption cross‐section described using two level approximation is highest for 5 b (115‐172 GM).

show abstract

“…Molecules with large second‐ and third‐order nonlinearity have outstanding impact in optical information technology, data storage, optical sensing, and opto‐electronic devices . The flow of electrons from the donor to acceptor through π‐conjugation in organic molecules results in intramolecular charge transfer (ICT), which is mainly influenced by electron‐donating and electron‐withdrawing nature of the functional groups . The imbalance between the donor (D) and acceptor (A) groups in molecules leads to the asymmetric spreading of electrons in one of the ground or in excited states, which switch the optical nonlinearity in molecules .…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical investigation of linear and nonlinear optical properties of ethyl‐3‐hydroxy‐2‐napthoate azo dyes by solvatochromic, computational aspects, and Z‐scan technique

Yadav

Taware

Sreenath³

et al. 2020

J of Physical Organic Chem

Self Cite

View full text Add to dashboard Cite

To investigate the effect of substituents in azo dyes on their nonlinear optical properties, four azo dyes were synthesized using ethyl‐3‐hydroxy‐2‐naphthoate as a coupler and characterized. The polarizability (α) and hyperpolarizability (β and γ) constants were determined by using solvatochromic and computational method. A group of global hybrid and range seperated hybrid functionals having different Hartree‐Fock exchange percentage were used to evaluate the NLO properties. The functional ωB97 and ωB97XD performed better in the determination of polarizability (α) and hyperpolarizability (β and γ), respectively. The observed results for polarizability and hyperpolarizability parameters were supported by highest occupied molecular orbital‐lowest unoccupied molecular orbital (HOMO‐LUMO) energy gap, Hammett‐coefficient (σ), excited‐state coefficients (σex), and hyper‐hardness (Γ) values. Third‐order NLO properties were analyzed by using Z‐scan technique. The –OCH3 substituted dye 4d shows higher value of molecular susceptibility (χ(3)), polarizability (α), and hyperpolarizability (β and γ) parameters among the studied azo dyes. They are likely to have the potential applications in optoelectronics and photonics.

show abstract

Carbazole-containing push–pull chromophore with viscosity and polarity sensitive emissions: Synthesis and photophysical properties

Cited by 29 publications

References 47 publications

Engineering a light-driven cyanine based molecular rotor to enhance the sensitivity towards a viscous medium

Engineering a light-driven cyanine based molecular rotor to enhance the sensitivity towards a viscous medium

N‐Ethyl Carbazole Derived D‐π‐A‐π‐D Based Fluorophores: Consolidated Spectroscopic, Viscosity and DFT Studies

Experimental and theoretical investigation of linear and nonlinear optical properties of ethyl‐3‐hydroxy‐2‐napthoate azo dyes by solvatochromic, computational aspects, and Z‐scan technique

Contact Info

Product

Resources

About