Synthesis, properties and photolysis of new iodonium tetrakis(pentafluorophenyl)gallate photoinitiators and comparison with their indate and aluminate analogs

Ren, Kun; Malpert, John H.; Gu, Haiyan; Li, Huiying; Neckers, Douglas C.

doi:10.1016/s0040-4020(02)00497-0

Cited by 12 publications

(8 citation statements)

References 13 publications

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“…Diphenyliodonium salts like ODPI are known to undergo photodissociation, whereby the molecule loses its positive charge and generates a proton (indeed, ODPI is an example of a "photoacid generator"). 32,33 In the present case, the protons are not responsible for the structural transition. All samples were prepared in buffer solution and the measured pH of the sample before and aer UV irradiation was almost the same at around 7.5.…”

Section: Vesicle To Micelle Transition Induced By Lightmentioning

confidence: 55%

“…It is further known that molecules such as ODPI lose their cationic charge by photodissociation when irradiated with ultraviolet (UV) light. 32,33 Thus, when ODPI-SDBS vesicles are exposed to UV light, the loss of charge on ODPI results in a transition from vesicles to spherical micelles (Fig. 1c).…”

Section: Introductionmentioning

confidence: 92%

“…We have considered an alternate possibility for the UV-induced PR effect, which is that reects the scission of hm-alginate chains due to radicals generated by photodissociation of ODPI. 32,33 To test this, we solubilized ODPI in micelles of the nonionic surfactant Triton X100 and added it to solutions of alginate and hm-alginate. No changes in viscosity were observed in these solutions upon UV irradiation.…”

Section: Vesicle To Micelle Transition Induced By Lightmentioning

confidence: 99%

“…Here, we present a simple design for photoresponsive vesicles that uses only molecules that are commercially available and relatively inexpensive. The impetus for our study was the observation that alkyl-substituted diaryliodonium salts, which are frequently used as cationic photoinitiators, 32,33 have an amphiphilic nature. In particular, we have worked with the molecule, p-octyloxydiphenyliodonium hexauoroantimonate (ODPI), 34,35 and we conrm that this molecule acts as a cationic surfactant.…”

Section: Introductionmentioning

confidence: 99%

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Light-induced transformation of vesicles to micelles and vesicle-gels to sols

Javvaji

Yaraghi

et al. 2013

Soft Matter

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Vesicles are self-assembled nanocontainers that are used for the controlled release of cosmetics, drugs, and proteins. Researchers have been seeking to create photoresponsive vesicles that could enable the triggered release of encapsulated molecules with accurate spatial resolution. While several photoresponsive vesicle formulations have been reported, these systems are rather complex as they rely on special light-sensitive amphiphiles that require synthesis. In this study, we report a new class of photoresponsive vesicles based on two inexpensive and commercially available amphiphiles. Specifically, we employ p-octyloxydiphenyliodonium hexafluoroantimonate (ODPI), a cationic amphiphile that finds use as a photoinitiator, and a common anionic surfactant, sodium dodecylbenzenesulfonate (SDBS). Mixtures of ODPI and SDBS form "catanionic" vesicles at certain molar ratios due to ionic interactions between the cationic and anionic headgroups. When irradiated with ultraviolet (UV) light, ODPI loses its charge and, in turn, the vesicles are converted into micelles due to the loss of ionic interactions. In addition, a mixture of these photoresponsive vesicles and a hydrophobically modified biopolymer gives a photoresponsive vesicle-gel. The vesicle-gel is formed because hydrophobes on the polymer insert into vesicle bilayers and thus induce a three-dimensional network of vesicles connected by polymer chains.Upon UV irradiation, the network is disrupted because of the conversion of vesicles to micelles, with the polymer hydrophobes getting sequestered within the micelles. As a result, the gel is converted to a sol, which manifests as a 40 000-fold light-induced drop in sample viscosity.

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Section: Vesicle To Micelle Transition Induced By Lightmentioning

confidence: 55%

Section: Introductionmentioning

confidence: 92%

Section: Vesicle To Micelle Transition Induced By Lightmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Light-induced transformation of vesicles to micelles and vesicle-gels to sols

Javvaji

Yaraghi

et al. 2013

Soft Matter

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show abstract

“…This unsatisfying finding is in agreement with the literature where the chemistry of the species of type [Ga(Ar) 4 ] À is nearly exclusively limited to the [Ga(C 6 F 5 ) 4 ] À anion. [54][55][56][57] Mes 3 Ga is an exceedingly weak Lewis acid and there are no stable adducts known with Lewis bases such as THF or Et 2 O. In contrast to the aluminiumtriorganyls (which form Lewis acid-base adducts immediately), the considerably reduced Lewis acidity of Ga(aryl) 3 results in a nearly trigonal planar arrangement around the gallium center with the mesityl groups in a propeller-like arrangement.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%