Photoinduced electron transfer for pyrenesulfonamide conjugates of tryptophan-containing peptides. Mitigation of fluoroprobe behavior in N-terminal labeling experiments

Jones, Guilford; Lu, Lily N.; Vullev, Valentine I.; Gosztola, David J.; Greenfield, Scott R.; Wasielewski, Michael R.

doi:10.1016/0960-894x(95)00416-q

Cited by 49 publications

(55 citation statements)

References 19 publications

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“…47,48 That is, multiple short and efficient "electron hopping" steps along arrays of redox moieties allow ET to exceed the 2-nm tunneling limit. [48][49][50][51][52] Deoxyribonucleic acid (DNA) strands represent a class of biopolymers that can mediate CT at distances exceeding 2 nm. [53][54][55][56][57] Short efficient tunneling steps between closely situated bases, with relatively negative reduction potentials of their radical cations, mediate hole hopping.…”

Section: Ct Molecular Electrets: Practical Ideas From Structural Biologymentioning

confidence: 99%

Bioinspired molecular electrets: bottom-up approach to energy materials and applications

2015

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Abstract. The diversity of life on Earth is made possible through an immense variety of proteins that stems from less than a couple of dozen native amino acids. Is it possible to achieve similar engineering freedom and precision to design electronic materials? What if a handful of nonnative residues with a wide range of characteristics could be rationally placed in sequences to form organic macromolecules with specifically targeted properties and functionalities? Referred to as molecular electrets, dipolar oligomers and polymers composed of non-native aromatic beta-amino acids, anthranilamides (Aa) provide venues for pursuing such possibilities. The electret molecular dipoles play a crucial role in rectifying charge transfer, e.g., enhancing charge separation and suppressing undesired charge recombination, which is essential for photovoltaics, photocatalysis, and other solar-energy applications. A set of a few Aa residues can serve as building blocks for molecular electrets with widely diverse electronic properties, presenting venues for bottom-up designs. We demonstrate how three substituents and structural permutations within an Aa residue widely alter its reduction potential. Paradigms of diversity in electronic properties, originating from a few changes within a basic molecular structure, illustrate the promising potentials of biological inspiration for energy science and engineering.

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Section: Ct Molecular Electrets: Practical Ideas From Structural Biologymentioning

confidence: 99%

Bioinspired molecular electrets: bottom-up approach to energy materials and applications

2015

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“…Free-moving charges in the electret or in the surrounding media would screen the dipolegenerated fields eliminating the dipole effect. Hence, electron tunneling is representative of the prevalent mechanism of CT mediated by biological and biomimetic polypeptide structures [37][38][39][40][41][42][43]. Tunneling, however, limits the distance of efficient CT to about 2 nm [37,38].…”

Section: Introductionmentioning

confidence: 99%

Building blocks for bioinspired electrets: molecular-level approach to materials for energy and electronics

Larsen

Espinoza

Hartman

et al. 2015

Pure and Applied Chemistry

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In biology, an immense diversity of protein structural and functional motifs originates from only 20 common proteinogenic native amino acids arranged in various sequences. Is it possible to attain the same diversity in electronic materials based on organic macromolecules composed of non-native residues with different characteristics? This publication describes the design, preparation and characterization of non-native aromatic β-amino acid residues, i.e. derivatives of anthranilic acid, for polyamides that can efficiently mediate hole transfer. Chemical derivatization with three types of substituents at two positions of the aromatic ring allows for adjusting the energy levels of the frontier orbitals of the anthranilamide residues over a range of about one electronvolt. Most importantly, the anthranilamide residues possess permanent electric dipoles, adding to the electronic properties of the bioinspired conjugates they compose, making them molecular electrets.

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“…Stern-Volmer analysis of bimolecular quenching indicates that dynamic quenching is approximately twice as efficient as static quenching. The results of fluorescence quenching measurements combined with cyclic voltammetry measurements of the BODIPY TMR redox potential yield convincing evidence for quenching via photoinduced charge transfer (Meinen et al, in preparation; [27][28][29][30][31]). In this process, collisions between Trp and the excited BODIPY TMR form a complex in which an electron is transferred from Trp to the hole in the BODIPY TMR S 0 state.…”

Section: Bodipy Tmr-tryptophan Interactionmentioning

confidence: 94%

Fluorescence probe of polypeptide conformational dynamics in gas phase and in solution

Iavarone¹,

Meinen²,

Schulze³

et al. 2006

International Journal of Mass Spectrometry

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Photoinduced electron transfer for pyrenesulfonamide conjugates of tryptophan-containing peptides. Mitigation of fluoroprobe behavior in N-terminal labeling experiments

Cited by 49 publications

References 19 publications

Bioinspired molecular electrets: bottom-up approach to energy materials and applications

Bioinspired molecular electrets: bottom-up approach to energy materials and applications

Building blocks for bioinspired electrets: molecular-level approach to materials for energy and electronics

Fluorescence probe of polypeptide conformational dynamics in gas phase and in solution

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