Effect of twisted molecular geometry on the solid-state emissions of an anthracene fluorophore

Sarma, Rupam; Gogoi, Gautomi

doi:10.1039/d3ce00481c

Cited by 3 publications

(4 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A similar observation was made for PTCS-2 with comparable spectral features. These spectral features are assigned to different transitions by comparing our results with the literature data. − TD-DFT computations were later employed to verify this assignment (vide infra).…”

Section: Resultsmentioning

confidence: 99%

“…From the comparison of various results, the twisted molecular geometry is beneficial for enhanced photoluminescence. 32 Nowadays, phenothiazine-based donor−acceptor systems have been explored for their applications in dye-sensitized solar cells, 33 fabrication OLED, 34 and sensors. 35 Phenothiazine (PTZ) is considered as an efficient functional unit to generate AIE, ICT, and stimuli-responsive effects attributed to its structural features, including nonplanar geometry and electrondonating capability.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Thus, the TICT phenomenon can be used as a design strategy for novel functional materials owing to the possibility of tuning the photophysical properties by appropriately introducing substituents and modifying the polar environment. From the comparison of various results, the twisted molecular geometry is beneficial for enhanced photoluminescence …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Intramolecular Charge Transfer and Stimuli-Responsive Emission in Cholesterol-Appended Phenothiazine–Cyanostyryl-Based Donor–Acceptor Systems

Athira,

Nelliyulla Kappumchalil,

Sachin

et al. 2024

J. Phys. Chem. A

View full text Add to dashboard Cite

Organic fluorescent molecules have received considerable attention owing to their various optoelectronic applications. Herein, we report the design and synthesis of two cholesterol-functionalized cyanostyrene-phenothiazine-based D–π–A systems that are emissive in both the solution and solid states. The newly synthesized cholesterol-appended phenothiazine-cyanostyrene diads PTCS-1 and PTCS-2 vary in the N-alkylation of phenothiazine, respectively, withoctyl andhexyl chains. Both molecules are highly fluorescent and show reasonably good quantum yields in nonpolar solvents because of twisted intramolecular charge transfer (TICT). The molecules exhibit aggregation-induced emission in the solid state. Due to the presence of flexible alkyl chains in the phenothiazine and cholesterol moieties, PTCS-1 and PTCS-2 show mechanochromic luminescence switching in response to external shear stress and emission recovery under methanol vapor. Powder X-ray diffraction studies prove that the emission switching on the applied stimuli in both PTCS-1 and PTCS-2 is attributed to the reversible transformation between the crystalline and amorphous states. Time-dependent density functional theory (TD-DFT) studies are carried out to gain insight into the ICT interactions. TD-DFT analysis at the TD-M06-2X/def2-TZVP level further revealed that in both molecules, the lowest unoccupied molecular orbital (LUMO) + 2, LUMO, highest occupied molecular orbital (HOMO), and HOMO – 1 orbitals are responsible for the charge transfer interactions. These ICT interactions are identified as π–π* type interactions.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Intramolecular Charge Transfer and Stimuli-Responsive Emission in Cholesterol-Appended Phenothiazine–Cyanostyryl-Based Donor–Acceptor Systems

Athira,

Nelliyulla Kappumchalil,

Sachin

et al. 2024

J. Phys. Chem. A

View full text Add to dashboard Cite

show abstract

“…Synthesis of Ant: Ant was synthesized by following a modified literature procedure. [46] Typically, a 100 mL round-bottom flask equipped with a magnetic stirrer and reflux condenser was charged with 9-Anthracenecarboxaldehyde (0.150 g, 9.86×10…”

Section: Methodsmentioning

confidence: 99%

Photoinduced Puffing with Large Volume Expansion and Photomechanical Motions induced by Topochemical [4+4] Reactions in Molecular Crystal Solvates

Giri,

Panda,

Panda

2024

Chemistry A European J

View full text Add to dashboard Cite

In this work, we report the first example of two crystal solvates of an anthracene‐benzhydrazide based molecule (Ant) that display very distinct photo‐responsive behaviour when 365 or 405 nm or visible light is illuminated. For the first time, the crystal hydrate that has water molecule in the lattice (hereafter named as Ant‐H2O) display fascinating puffing behavior with large volume expansion and surface modulation when illuminated with 405 nm light, a phenomenon very much similar to the rice or popcorn puffing by thermal treatment. Utilizing the properties of photoconverted Ant‐H2O crystals, we have demonstrated their application in photoinduced enhanced liquid absorption using various liquids/solutions.The other crystal solvate having DMF in the crystal lattice (hereafter named as Ant‐DMF) responds to 405 nm light by bending, twisting, chopping, jumping or splitting etc. The chopping of Ant‐DMF crystal was also observed under ambient / white light but at a slower rate compared to 405 nm light. Single crystal X‐ray diffraction study reveals that the photoinduced puffing and photomechanical effects of these materials are rooted to the topochemical [4+4] cycloaddition reaction between the anthracene moieties that facilitate molecular packing change assisted by the reconfiguration of intermolecular non‐covalent interactions involving lattice trapped solvent molecules.

show abstract

Versatile aggregation induced emissive molecular probes incorporating different donor/acceptor groups for tunable multiple color fluorescence

Mathivanan,

Villaman,

Shanmugaraj

et al. 2024

Dyes and Pigments

View full text Add to dashboard Cite

Effect of twisted molecular geometry on the solid-state emissions of an anthracene fluorophore

Abstract: Anthracene-derived luminogen, A-4OH, obtained by reacting anthracene-9-aldehyde with 4-hydroxy benzoic acid hydrazide, produced two polymorphic phases and two solvates, each of which could be distinguished by the solid state emission....

Cited by 3 publications

References 51 publications

Intramolecular Charge Transfer and Stimuli-Responsive Emission in Cholesterol-Appended Phenothiazine–Cyanostyryl-Based Donor–Acceptor Systems

Intramolecular Charge Transfer and Stimuli-Responsive Emission in Cholesterol-Appended Phenothiazine–Cyanostyryl-Based Donor–Acceptor Systems

Photoinduced Puffing with Large Volume Expansion and Photomechanical Motions induced by Topochemical [4+4] Reactions in Molecular Crystal Solvates

Versatile aggregation induced emissive molecular probes incorporating different donor/acceptor groups for tunable multiple color fluorescence

Contact Info

Product

Resources

About