Protecting a Squaraine near-IR Dye through Its Incorporation in a Slippage-Derived [2]Rotaxane

Hsueh, Sheng-Yao; Lai, Chien‐Chen; Liu, Yi-Hung; Wang, Yu; Peng, Shie‐Ming; Chiu, Sheng‐Hsien

doi:10.1021/ol702050w

Cited by 63 publications

(13 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A potential issue with this protocol is that the macrocycles could be cross-linked in a random manner instead of being trapped convergently, making suitane synthesis a challenging goal to reach. Rotaxanes can also be synthesized (Scheme c) by the use of a strategy called slippage. − We envisioned that a similar strategy can be applied to the preparation (Scheme d) of suitanes, wherein the suit opens up entrances to its cavity at high temperatures so that the torso slips inside. At low temperatures, the cyclophane closes its portals, and the torso is mechanically interlocked within the cyclophane.…”

mentioning

confidence: 99%

Suit[4]ane

Liu

Stern

2020

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Suitanes are two-component mechanically interlocked molecules in which one (torso) of the components, with several protruding limbs, is encompassed by another (suit) all-in-one component. This kind of molecular ship-in-a-bottle architecture remains a challenging one to make. Herein, we report a porphyrin-based suit[4]ane, which is composed of a porphyrin with four protruding ligands (two phenyl groups and two bromine atoms) called the limbs that are encompassed by a tricyclic octacationic cyclophane. The suit[4]ane can be obtained by slippage, a mechanism by which the cyclophane is able to open up two of its entrances in order to take up the porphyrin at high temperature and close them down at low temperature, locking the porphyrin inside its binding cavity. Dynamic 1H NMR spectroscopy reveals that the trapped porphyrin inside the cyclophane rocks back and forth in the suit[4]ane about 1000 times a second.

show abstract

mentioning

confidence: 99%

Suit[4]ane

Liu

Stern

2020

J. Am. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…If either component of ammonium phosphate was chemisorbed onto the surface of the PMPS particles, then the particles, either before or after compounding into polymer fibres, would not consistently leach phosphate over numerous washing events. However, there is evidence, in two previously reported X-ray crystal structures, that squarate oxygen atoms are capable of co-ordination with metals (Hsueh et al., 2007a,b). Thus, direct metal co-ordination with the squarate oxygens in the PMPS pores must also be taken into account, which is suspected, in corporation with the specific pore sizes, to give rise to the differences in metal element uptake.…”

Section: Resultsmentioning

confidence: 99%

The uptake of metal elements into poly(1-methylpyrrol-2-ylsquaraine) particles and a study of their porosity

Lynch¹,

Bennett

Bateman

et al. 2016

Adsorption Science & Technology

View full text Add to dashboard Cite

The article reports an experimental study of the metal uptake properties of poly(1-methylpyrrol-2-ylsquaraine) particles, in the context of 51 elemental metal complexes. Vagaries of the experimental results meant that the final analysis took place for 43 of these metals. After an initial descriptive analysis, an Analysis of Variance model was fitted. This revealed that several factors, some intrinsic to the metals themselves, others relating to the experimental conditions, have an important influence on the adsorption characteristics of the poly(1-methylpyrrol-2-ylsquaraine) particles. Of these, the most important is the ratio of the number of moles of the metal to the number of moles of the adsorbent particles. X-ray mapping of the poly(1-methylpyrrol-2-ylsquaraine) particles treated with contrast agent revealed that, although adsorption was all throughout the particles, the majority of the agent was adsorbed within 10-15% (diameter distance) of the surface of the particles.

show abstract

“…[29][30][31][32] Another class of compounds centers on the cyclic oxobutanal ring and is referred to as squaraine or squaric acid fluorophores. 33 The extreme electrophilicity of this cyclic butane ring is susceptible to nucleophilic attack, which irreversibly diminishes the optical properties of the compound, unless the core is protected by one of several methods including rotaxane encapsulation 34 which reduces the overall applicability in small molecule bioimaging. Contrary to the squaraine class of fluorophores, the tricyclic fused structures of phenoxazine and phenothiazine are highly structurally and optically stable even in the presence of nucleophilic species due to the aromatic core.…”

Section: Classes Of Nir Fluorophoresmentioning

confidence: 99%

NIR fluorescent small molecules for intraoperative imaging

Owens

Lee

Choi

et al. 2015

WIREs Nanomed Nanobiotechnol

View full text Add to dashboard Cite

Recent advances in bioimaging and nanomedicine have permitted the exploitation of molecular optical imaging in image-guided surgery; however, the parameters mediating optimum performance of contrast agents are not yet precisely determined. To develop ideal contrast agents for image-guided surgery, we need to consider the following criteria: 1) excitation and emission wavelengths in the NIR window, 2) optimized optical characteristics for high in vivo performance, 3) overcoming or harnessing biodistribution and clearance, and 4) reducing nonspecific uptake. The design considerations should be focused on optimizing the optical and physicochemical property criteria. Biodistribution and clearance should first be considered because they mediate the fate of a contrast agent in the body such as how long after intravenous injection a contrast agent reaches the peak signal-to-background ratio (SBR) and how long the signal lasts (retention).

show abstract

Protecting a Squaraine near-IR Dye through Its Incorporation in a Slippage-Derived [2]Rotaxane

Abstract: The photophysical properties and chemical stability of a squaraine derivative were enhanced after using Na+ ions to template a high-yield slippage synthesis of a [2]rotaxane from the dye and a molecular cage.

Cited by 63 publications

References 11 publications

Suit[4]ane

Suit[4]ane

The uptake of metal elements into poly(1-methylpyrrol-2-ylsquaraine) particles and a study of their porosity

NIR fluorescent small molecules for intraoperative imaging

Contact Info

Product

Resources

About