Cover Picture: Scaffold‐Optimized Dendrimers for the Detection of the Triacetone Triperoxide Explosive Using Quartz Crystal Microbalances (ChemPlusChem 2/2012)

Lubczyk, Daniel; Grill, Matthias; Baumgarten, Martin; Waldvogel, Siegfried R.; Müllen, Kläus

doi:10.1002/cplu.201290006

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“…The unsubstituted polyphenylene dendrimer Td-G2 (Scheme ) was synthesized according to ref, the functionalized dendrimers Td-G2-(Phenyl) 8 , Td-G2-(NO2) 8 , Td-G2-(CN) 8 , Td-G2-(COOH) 6 , Td-G2-(COOMe) 8 , and TD-G2-(pyridyl) 16 (see Scheme ) were synthesized according to refs , , and . All guest molecules were obtained from Sigma-Aldrich Chemical GmbH (Germany) and used without further purification (Scheme ).…”

Section: Experimental Sectionmentioning

confidence: 99%

“…19 Pyridine-functionalized polyphenylene dendrimers were proven to take up triacetone triperoxide (TATP) especially well and to serve as highly sensitive detector. 20 All these studies were shown to depend critically on the nature of the guest molecules as strong variations of the amounts being taken up from the gas phase occurred. However, quartz crystal microbalance only allows one to quantify the uptake from the gas phase, and is not applicable for solution processes such as for example the loading of drugs into dendrimers.…”

Section: ■ Introductionmentioning

confidence: 99%

“…These voids can be used to adsorb small guest molecules from the gas phase, as was shown by gravimetric measurements with a quartz crystal microbalance (QCM) in which the PPD S were applied as active layers for monitoring their interaction with volatile organic compounds (VOCs) . Pyridine-functionalized polyphenylene dendrimers were proven to take up triacetone triperoxide (TATP) especially well and to serve as highly sensitive detector . All these studies were shown to depend critically on the nature of the guest molecules as strong variations of the amounts being taken up from the gas phase occurred.…”

Section: Introductionmentioning

confidence: 99%

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Guest Uptake by Rigid Polyphenylene Dendrimers Acting As a Unique Dendritic Box in Solution Proven by Isothermal Calorimetry

et al. 2013

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The existence of a dendritic box in polyphenylene dendrimers is demonstrated by isothermal titration calorimetry (ITC). The thermodynamic parameters of the uptake process of a variety of small guest molecules into the dendrimers are measured. ITC revealed that for dendrimers with an unpolar interior this process is mainly entropically driven. Two processes have been elucidated for the entropy gain: (i) the release of solvent molecules which solvate the guests and (ii) solvent molecules in the voids of the dendrimers which are replaced by the guests. For dendrimers which are substituted with polar functionalities in the core, enthalpic effects become more dominant as some hydrogen bonds and π–π-interaction come into play. Because of the rigidity of the dendrimer host, these less specific interactions can only occur in the core of the differently functionalized interior of the dendrimers since the surface is the same all over. Thereby, it is evidenced that guest molecules can be selectively trapped inside the dendrimer and not on the surface. For different host–guest pairs ITC resulted in characteristic thermodynamic parameters for the uptake. These values might give guidelines to estimate and model the binding strength and the release properties between a drug and dendritic carrier.

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Section: Experimental Sectionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%