Solvent dependent isomerization of photochromic dithienylethenes: synthesis, photochromism, and self-assembly

Sen, Choong Ping; Valiyaveettil, Suresh

doi:10.1039/c6ra21348k

Cited by 5 publications

(6 citation statements)

References 40 publications

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“…Compared to the open isomer, the increased rigidity of the closed isomer might restrict the ring-shaped structure formation accompanied with stabilization by smaller self-assembly with size range 75-110 nm (Figure S19b). [60] The formation of the self-assembly can be correlated to several possible intermolecular interactions present in our system, such as: a) π-π interactions of NDI; [61] b) non-classical Hbonding of CÀ H of triazole unit. [62] The self-assembled behavior was further investigated with increasing percentage of water in THF solution.…”

Section: Photophysical Studiesmentioning

confidence: 92%

Non‐Conjugated Bis‐(Dithienylethene)‐Naphthalenediimide as a Dynamic Anti‐Counterfeiting Agent: Driving the Wheel of Photoswitching Enactment

Bag

Karmakar

Mondal

et al. 2023

Chemistry A European J

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Photochromic fluorescent molecules dramatically extend their fields of applications ranging from optical memories, bioimaging, photoswitches, photonic devices, anti‐counterfeiting technology and many more. Here, we have logically designed and synthesized a triazole appended bis‐(dithienylethene)‐naphthalenediimide based photo‐responsive material, 5, which demonstrated fluorescence enhancement property upon photocyclization (ΦF=0.42), with high photocyclization (44 s, ksolution=0.0355 s−1, ksolid=0.0135 s−1) and photocycloreversion (160 s, ksolution=0.0181 s−1, ksolid=0.0085 s−1) rate and decent photoreaction quantum yield (Φo→c=0.93 and Φc→o=0.11). The open isomer almost converted to the closed isomer at photo‐stationary state (PSS) with distinct color change from colorless to blue with 92.85 % conversion yield. A reversible noninvasive modulation of fluorescence through efficient photoinduced electron transfer (PET) process was observed both in solution as well as in solid state. The fluorescence modulation through PET process was further corroborated with thermodynamic calculations using the Rehm–Weller equation and quantum chemical studies (DFT). The thermally stable compound 5 exhibits high fatigue resistance property (up to 50 cycles) both in solution and solid state. Furthermore, the compound 5 was successfully applied as erasable ink and in deciphering secret codes (Quick Response/bar code) portending potential promising application in anti‐counterfeiting.

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Section: Photophysical Studiesmentioning

confidence: 92%

Non‐Conjugated Bis‐(Dithienylethene)‐Naphthalenediimide as a Dynamic Anti‐Counterfeiting Agent: Driving the Wheel of Photoswitching Enactment

Bag

Karmakar

Mondal

et al. 2023

Chemistry A European J

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“…DTE-containing multiphotochromic hybrids. [58][59][60] A multiphotochromic system reported by Feringa and coworkers illustrates the interesting utility of DTE for light-gated photochromism. [61] When a DTE unit is connected to an overcrowded alkene-based rotary motor via an ethynylene linkage, 6, operation of the motor becomes dependent on the isomerization state of the DTE (Figure 7).…”

Section: Multiphotochromic Systemsmentioning

confidence: 93%

“…Another DTE‐AZB hybrid, 4 , with ethynylene junctions, reported by Valiyaveettil et al, showed solvent‐dependent photochromic behavior. [ 59 ] Selective ring closure of the DTE core occurs upon irradiation at 365 nm in chloroform; at the same wavelength, concurrent DTE ring closure and E → Z photoisomerization of AZB proceed in THF. For both DTE‐AZB hybrids, selective maneuvering of the distinct chromophores is inefficient, and not all switchable states are addressable.…”

Section: Molecular Switches and Motors Activated By Multiple Orthomentioning

confidence: 99%

Molecular Switches and Motors Powered by Orthogonal Stimuli

2020

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Synthetic molecular machines are designed to undergo specific nanoscale movements in response to specific physical or chemical stimuli. The “engines” of molecular machines responsible for their motion are usually presented by molecular switches and motors that undergo predetermined shape transformations upon appropriate stimulation. Various types of molecular switches and motors activated by different stimuli, such as light irradiation or chemical input, have been devised and used as the core of mechanically active molecular systems. However, despite extensive research, the structural and functional complexity of state‐of‐the‐art synthetic molecular machines does not rival that of biological or human‐scale counterparts. The most apparent difference is that current molecular machines show only limited modes of translational, rotational, and oscillatory motion that are typically triggered by a single stimulus. A promising strategy for achieving more elaborate movement is to integrate multiple active parts that can be manipulated by orthogonal stimuli. However, this approach is often complicated by mutual interference between the components or between stimuli. In this review, we survey recent notable progress in the development of molecular switches and motors that exhibit distinct modes of movement triggered by orthogonal stimuli. Though this approach is challenging, it may provide insights about the innovation needed to develop next‐generation molecular machines with improved maneuverability and more sophisticated functions.

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“…The conversion of 22 to 6a was performed using a modified procedure reported by Sen and Valiyaveettil. 15 Thus, bromide 22 was treated with 1.1 equiv of B 2 pin 2 in the presence of 5 mol% Pd(dppf)Cl 2 •CH 2 Cl 2 and 3.0 equiv of potassium acetate in 1,4-dioxane at 80 °C for 14 h to provide pinacol borate 6a in 84% yield. Cl 2 •CH 2 Cl 2 (5 mol%), B 2 pin 2 (1.1 equiv), KOAc (3.0 equiv), 1,4-dioxane, 80 °C, 14 h (84% 23a in 59% yield.…”

Section: Methodsmentioning

confidence: 99%

“…13 C NMR (126 MHz, CDCl 3 ): δ 28. 4, 56.4, 71.0, 80.3, 106.1, 111.2, 112.4, 127.5, 127.8, 128.5, 131.9, 136.9, 145.7, 148.5, 153. (15). Under an argon atmosphere, NBS (4.45 g, 25.0 mmol) was added portionwise to a solution of 14 (7.49 g, 22.7 mmol) in THF (140 mL) at −78 °C.…”

Section: -Benzyloxy-1-methoxy-4-nitrobenzene (12)mentioning

confidence: 99%

Divergent Total Synthesis of Azalamellarins D and N

Fukuda¹,

Okutani²,

Sumi³

et al. 2021

HETEROCYCLES

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Lamellarins are polycyclic marine alkaloids with potent cytotoxic activities against cancer cell lines. A divergent synthesis of azalamellarins D and N, lactam congeners of the marine natural products lamellarins D and N, has been achieved via the pentacyclic 14-bromo-8,9-dihydro-benzo[7,8]indolizino[3,2-c]quinolin-6(5H)-one intermediate. The pentacyclic intermediate can be synthesized from methyl 1-(benzensulfonyl)-3-bromo-1H-pyrrole-2-carboxylate via the Suzuki-Miyaura cross-coupling and intramolecular direct arylation as key reactions.

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Solvent dependent isomerization of photochromic dithienylethenes: synthesis, photochromism, and self-assembly

Abstract: The self-assembly of photochromic dithienylethene molecules into circular nanostructures is reported. The formation of nanostructures is dependent on factors such as photoisomerization, solvent, and hydrogen bonding.

Cited by 5 publications

References 40 publications

Non‐Conjugated Bis‐(Dithienylethene)‐Naphthalenediimide as a Dynamic Anti‐Counterfeiting Agent: Driving the Wheel of Photoswitching Enactment

Non‐Conjugated Bis‐(Dithienylethene)‐Naphthalenediimide as a Dynamic Anti‐Counterfeiting Agent: Driving the Wheel of Photoswitching Enactment

Molecular Switches and Motors Powered by Orthogonal Stimuli

Divergent Total Synthesis of Azalamellarins D and N

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