Rapid UV Light‐Triggered Macromolecular <i>Click</i> Conjugations via the Use of <i>o</i>‐Quinodimethanes

Gruendling, Till; Oehlenschlaeger, Kim K.; Frick, Elena; Glaßner, Mathias; Schmid, Christina; Barner‐Kowollik, Christopher

doi:10.1002/marc.201100159

Cited by 104 publications

(122 citation statements)

References 47 publications

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“…The simplicity and versatility of the photoreactions are such that the sequence order and functionality within the chains can be arbitrarily varied. Our approach rests on a sole photochemical reaction relying on benzaldehyde species, which when irradiated lead to reactive dienes (so-called ‘photo-caged dienes')54 with an ortho -quinodimethane structure. Combined with ene reactive functional molecules, we reach diverse decamers from a library of six monomers.…”

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Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

et al. 2016

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Designing artificial macromolecules with absolute sequence order represents a considerable challenge. Here we report an advanced light-induced avenue to monodisperse sequence-defined functional linear macromolecules up to decamers via a unique photochemical approach. The versatility of the synthetic strategy—combining sequential and modular concepts—enables the synthesis of perfect macromolecules varying in chemical constitution and topology. Specific functions are placed at arbitrary positions along the chain via the successive addition of monomer units and blocks, leading to a library of functional homopolymers, alternating copolymers and block copolymers. The in-depth characterization of each sequence-defined chain confirms the precision nature of the macromolecules. Decoding of the functional information contained in the molecular structure is achieved via tandem mass spectrometry without recourse to their synthetic history, showing that the sequence information can be read. We submit that the presented photochemical strategy is a viable and advanced concept for coding individual monomer units along a macromolecular chain.

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Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

et al. 2016

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“…The product was obtained as a highly viscous yellowish oil (1. 22 13 General Procedure for ADMET Polymerizations. Monomer 3 and the selected chain-stopper (4, 5, P5) were weighed into a Supelco conical vial.…”

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Highly Orthogonal Functionalization of ADMET Polymers via Photo-Induced Diels–Alder Reactions

et al. 2012

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Within the current contribution, we introduce two strategies for the catalyst-free, modular, ambient temperature synthesis of ABC triblock copolymers via photoinduced Diels− Alder reactions. On the one hand, the 2-formyl-3-methylphenoxy (FMP) moiety (a second generation photoenol precursor) was employed for orthogonal polymer−polymer conjugations using terminal acrylates of diblock copolymers synthesized via acyclicdiene-metathesis (ADMET) polymerizations to directly prepare triblock copolymers. On the other hand, the disparate reactivity of 2,5-dimethylbenzophenone (first generation photoenol) and the FMP moiety was exploited to selectively synthesize complex triblock copolymers (6.5 kDa≤ M n ≤11.5 kDa, 1.16≤ PDI ≤ 1.30) via a sequential one pot approach utilizing the extraordinary orthogonality of the photoinduced Diels−Alder reaction. Polymers functionalized with a photoenol (second generation) moiety were employed for conjugation reactions with polymers featuring an acrylate terminus, while polymers having a photoenol (first generation) end group were employed for selective conjugations of maleimide functional polymers. In this context, the selective head-to-tail ADMET polymerization was employed as a straightforward methodology for the preparation of bifunctional polymers having a terminal acrylate and a photoenol end-group.

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“…[9] The latter strategy fulfills the harsh set of click conditions required for polymer-polymer ligation.…”

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Adding Spatial Control to Click Chemistry: Phototriggered Diels–Alder Surface (Bio)functionalization at Ambient Temperature

et al. 2011

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Rapid UV Light‐Triggered Macromolecular Click Conjugations via the Use of o‐Quinodimethanes

Cited by 104 publications

References 47 publications

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

Highly Orthogonal Functionalization of ADMET Polymers via Photo-Induced Diels–Alder Reactions

Adding Spatial Control to Click Chemistry: Phototriggered Diels–Alder Surface (Bio)functionalization at Ambient Temperature

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