Gated photochromism in azobenzene-appended rhodamine cassette: through-bond energy transfer – a universal strategy towards “Lock and Unlock” system

Raman, Arunachalam; George, Augustine; Ayyadurai, Niraikulam; Easwaramoorthi, Shanmugam

doi:10.1039/c8tc04170a

Cited by 19 publications

(21 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Next, a bromination reaction was performed at position 5 of the corresponding olefin in the imidazole ring (Im) to yield 2 . Finally, aniline was introduced via a Suzuki–Miyaura coupling reaction utilizing an arylboronate ester, 3 , in the presence of a palladium catalyst to yield reddish INA–AN , which had a curved structure between imidazonaphthyridine and the phenyl ring in aniline (An). The analogue INA–DMA was prepared by following the aforementioned procedure utilizing 4 …”

Section: Results and Discussionmentioning

confidence: 99%

High-Z′ Crystal Structure of Tricyclic Imidazonaphthyridine Derivatives and the Thermal Profiles of Their Polymorphs

Matsumoto

Umeno

Usui

et al. 2021

Crystal Growth & Design

View full text Add to dashboard Cite

The crystal structures and thermal profiles of three crystal polymorphs of tricyclic imidazonaphthyridine derivatives (INA) were investigated. The aniline derivative INA−AN, in which a 4-anilino moiety was introduced at position 9 of the imidazonaphthyridine framework, yielded a nonplanar curved structure between imidazonaphthyridine and aniline. Three crystals (INA−AN-α (I4 1 /a with Z′ = 1) as an emissive polymorph, as well as INA−AN-β1 and INA−AN-β2 (Pc with Z′ = 4) as nonemissive polymorphs) were obtained. The polymorphs comprised multiple-hydrogen-bond networks. INA−AN-β1 and -β2 crystallized into different polymorphs via recrystallization: INA−AN-β1 and -β2 were obtained from the solvent, as well as via melting and recrystallization processes. Notably, the crystal structures and parameters of INA−AN-β1 and -β2 largely corresponded, although their thermal behaviors were significantly different: INA−AN-β1 underwent a thermal crystal transformation, yielding INA−AN-α at ∼185 °C, while INA−AN-β2 readily melted at ∼190 °C. These distinct profiles indicated that the subtle distinct molecular arrangements, as well as crystal packings, might account for the different thermal profiles of INA−INA-β polymorphs. Interestingly, in addition to INA−AN-β polymorphs, an imidazonaphthyridine framework bearing an N,N-dimethylamine moiety, INA−DMA, crystallized in the P1̅ space group with Z′ = 4, indicating that the INA framework containing an aromatic ring afforded high-Z′ crystal structures.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

High-Z′ Crystal Structure of Tricyclic Imidazonaphthyridine Derivatives and the Thermal Profiles of Their Polymorphs

Matsumoto

Umeno

Usui

et al. 2021

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…34 Gated photochromism is a kind of photochromism where either one or both photoactive forms are converted (gated) reversibly into a third form (photo-inert) by external inputs like metal ion, heat, electric potential, etc. 35 Here, factors like metal ion, heat, potential, etc. behave like a gate pass.…”

Section: ■ Structural Features and Physicochemical And Photophysical ...mentioning

confidence: 99%

“…Here, the neighboring anthracene part showed a strong π−π interaction (noncovalent interaction), which affected the photophysical properties of the material. The group introduced the concept of free volume in In the same year (2018), Prof. Ayyadurai's research group from India 35 coupled azobenzene (donor) with rhodamine moiety (acceptor) through acetamide linkage (Figure 14) to develop a fruitful donor−acceptor system that is capable of exhibiting gated photochromism via the through-bond energytransfer (TBET) process. TBET facilitates the complexation of Fe 3+ and decomplexation by F − [tetrabutylammonium fluoride (TBAF)] reversibly.…”

Section: ■ Structural Features and Physicochemical And Photophysical ...mentioning

confidence: 99%

“…In the same year (2018), Prof. Ayyadurai’s research group from India coupled azobenzene (donor) with rhodamine moiety (acceptor) through acetamide linkage (Figure ) to develop a fruitful donor–acceptor system that is capable of exhibiting gated photochromism via the through-bond energy-transfer (TBET) process. TBET facilitates the complexation of Fe 3+ and decomplexation by F – [tetrabutylammonium fluoride (TBAF)] reversibly.…”

Section: Photochromismmentioning

confidence: 99%

See 1 more Smart Citation

A Brief Review on Advances in Rhodamine B Based Chromic Materials and Their Prospects

Bar

Chowdhury

2022

ACS Appl. Electron. Mater.

View full text Add to dashboard Cite

Chromic (stimuli-responsive reversible color change in the visible region) materials have been used in a number of commercial outlets with increasing demands. It is an important scientific issue and research hot spot in recent years simply due to its huge prospects. It includes the following: (i) photochromics in sunglasses, probes, optical data storage, molecular logic-gate and keypad lock, photopatterning, and photoprinting; (ii) thermochromics in paints, inks, architecture, molecular thermometers, and cotton fabrics; (iii) mechnochromics in plastics, textiles, and anticounterfeiting systems; (iv) electrochromics in switchable glass, smart paper strips, and flexible electronics; (v) halochromics in digital image colorimetry and acid−base indicators; (vi) ionochromics in colorimetric sensors and complexometric indicators; and (vii) hydrochromics in water-jet printing. The well-known rhodamine B (RhB) dye has now been considered a unique stimuli-dependent chromic material by researchers because of its outstanding photophysical and physicochemical properties that are suitable for real applications. In this review work, almost all of the works published on RhB-based stimuli-responsive materials from 1977 to 2022 have been studied critically, and significant progress is arranged in chronological order. In addition, an attempt has been made to show the prospects of what they can do in human service in the near future.

show abstract

“…Due to their remarkable colour change after light stimulation, photochromic materials could be used in the preparation of molecular switches [2], optical data storage [6], molecular logic gates [6] and colorimetric chemo-sensors [7], etc. To date, organic photochromic materials with core structures such as diarylethene [8,9], rhodamine [10][11][12][13], spiropyran [14][15][16] and azobenzene [4,17] have been developed. Among those reported photochromic materials, rhodamine derivatives have received significant attention in consideration of their outstanding advantages such as simple synthesis, distinctive colour change and good recoverability.…”

Section: Introductionmentioning

confidence: 99%

A Cu ²⁺ triggered reversible photochromic system: the structure photochromic response relationship study and potential applications

Wang

et al. 2023

R. Soc. open sci.

View full text Add to dashboard Cite

Fifteen rhodamine B hydrazide hydrazone (RhBHH) derivatives (compounds a – o ) with various substituent groups at different position and their photochromic property triggered by Cu 2+ were studied to illustrate the structure photochromic response relationship (SPRR). Three of them (compounds f – h ) with a para -position hydroxyl group and two meta -position halogen substituents display Cu 2+ -triggered photochromic which is significantly different from the previous reports. It was found that halogen atoms, which were generally considered to have no remarkable regulation effect, exhibited great influences on the photochromic behaviour of RhBHH derivatives. Detail photochromic properties of the developed photochromic system were revealed by using compound g as the model substrate, and only Cu 2+ displayed high selective trigger effect. Good reversible photochromic phenomenon was observed after stimulated with visible light irradiation and dark (or heat) bleaching consecutively. Furthermore, this photochromic system could be used in the preparation of photochromic glass, special security ink, molecular logic gate and two-dimensional code for security information storage.

show abstract

Gated photochromism in azobenzene-appended rhodamine cassette: through-bond energy transfer – a universal strategy towards “Lock and Unlock” system

Abstract: A dyad 1 comprising fluorescent rhodamine and photochromic azobenzene covalently linked through a phenylene bridge, which still retains their individual electronic properties, was synthesized.

Cited by 19 publications

References 25 publications

High-Z′ Crystal Structure of Tricyclic Imidazonaphthyridine Derivatives and the Thermal Profiles of Their Polymorphs

High-Z′ Crystal Structure of Tricyclic Imidazonaphthyridine Derivatives and the Thermal Profiles of Their Polymorphs

A Brief Review on Advances in Rhodamine B Based Chromic Materials and Their Prospects

A Cu ²⁺ triggered reversible photochromic system: the structure photochromic response relationship study and potential applications

Contact Info

Product

Resources

About

Gated photochromism in azobenzene-appended rhodamine cassette: through-bond energy transfer – a universal strategy towards “Lock and Unlock” system

Abstract: A dyad 1 comprising fluorescent rhodamine and photochromic azobenzene covalently linked through a phenylene bridge, which still retains their individual electronic properties, was synthesized.

Cited by 19 publications

References 25 publications

High-Z′ Crystal Structure of Tricyclic Imidazonaphthyridine Derivatives and the Thermal Profiles of Their Polymorphs

High-Z′ Crystal Structure of Tricyclic Imidazonaphthyridine Derivatives and the Thermal Profiles of Their Polymorphs

A Brief Review on Advances in Rhodamine B Based Chromic Materials and Their Prospects

A Cu 2+ triggered reversible photochromic system: the structure photochromic response relationship study and potential applications

Contact Info

Product

Resources

About

A Cu ²⁺ triggered reversible photochromic system: the structure photochromic response relationship study and potential applications