Mild synthesis and photophysical properties of symmetrically substituted diketopyrrolopyrrole derivatives

Zhang, Guanjun; Song, Longfeng; Bi, Shiming; Wu, Yue; Yu, Jianjun; Wang, Limin

doi:10.1016/j.dyepig.2013.10.025

Cited by 16 publications

(8 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Few attempts to solubilize DPP frameworks in aqueous solutions have been made, although some published strategies are based on the site‐specific introduction of short polyethylene glycol chains through N‐alkylation of both lactam moieties 4. 5 Further conjugation of such a non‐ionic DPP dye to a cell‐penetrating peptide [HIV‐I Tat (44‐61) fragment]4b or a porphyrin4d has been achieved, thus providing a two‐photon fluorescent tag suitable for live‐cell microscopy and photodynamic therapy. Also, water‐soluble conjugated and multicationic fluorene‐DPP polymers have been used for the detection of DNA by fluorescence techniques 6.…”

Section: Methodsmentioning

confidence: 99%

Identification of Core Segment of Amyloidal Peptide Mediated by Chaperone Molecules by using Scanning Tunneling Microscopy

Yang

Wang

2015

ChemPhysChem

View full text Add to dashboard Cite

We illustrate in this work that pristine assemblies of amyloidal peptides can be obtained by perturbations of reduced scanning bias, and show a broad distribution in peptide length. In contrast, the chaperone-mediated peptide co-assembly presents ordered lamellar structures with a homogeneous distribution in length, which could be attributed to the core segment of the peptide. The efforts are beneficial for gaining insight into the aggregation propensity of peptides and inter-peptide interactions.

show abstract

Section: Methodsmentioning

confidence: 99%

Identification of Core Segment of Amyloidal Peptide Mediated by Chaperone Molecules by using Scanning Tunneling Microscopy

Yang

Wang

2015

ChemPhysChem

View full text Add to dashboard Cite

show abstract

“…24b). 45 In THF, these derivatives (67, 68, 69, and 70) exhibited absorption bands at 496 nm, 485 nm, 482 nm, and 470 nm. The green emission bands of these derivatives in THF were located at 575 nm, 555 nm, 530 nm, and 527 nm.…”

Section: Structurally Modified Dpp-based Near-infrared (Nir) Dyesmentioning

confidence: 96%

Diketopyrrolopyrrole: brilliant red pigment dye-based fluorescent probes and their applications

2015

View full text Add to dashboard Cite

The development of fluorescent probes for the detection of biologically relevant species is a burgeoning topic in the field of supramolecular chemistry. A number of available dyes such as rhodamine, coumarin, fluorescein, and cyanine have been employed in the design and synthesis of new fluorescent probes. However, diketopyrrolopyrrole (DPP) and its derivatives have a distinguished role in supramolecular chemistry for the design of fluorescent dyes. DPP dyes offer distinctive advantages relative to other organic dyes, including high fluorescence quantum yields and good light and thermal stability. Significant advancements have been made in the development of new fluorescent probes based on DPP in recent years as a result of tireless research efforts by the chemistry scientific community. In this tutorial review, we highlight the recent progress in the development of DPP-based fluorescent probes for the period spanning 2009 to the present time and the applications of these probes to recognition of biologically relevant species including anions, cations, reactive oxygen species, thiols, gases and other miscellaneous applications. This review is targeted toward providing the readers with deeper understanding for the future design of DPP-based fluorogenic probes for chemical and biological applications.

show abstract

“…32 Gruber et al investigated the effect of linear and branched side chains on the thin-film structure and electrical properties of DPP-based polymers. 33 Examples of DPP conjugates that are processable in aqueous condition are much rarer, [37][38][39][40][41][42][43] and out of those, DPP-peptide conjugates have not been extensively explored. [37][38][39] Draper et al prepared conductive hydrogels by conjugating phenylalanine to the amide functionalities of a thiophene-conjugated DPP core.…”

Section: Introductionmentioning

confidence: 99%

Aqueous Self-Assembly of Peptide–Diketopyrrolopyrrole Conjugates with Variation of N-Alkyl Side Chain and π-Core Lengths

Panda

Tovar

2021

Organic Materials

View full text Add to dashboard Cite

Peptidic sequences when conjugated to π-electronic groups form self-assembled networks of π-electron pathways. These materials hold promise for bio-interfacing charge transporting applications because of their aqueous processability and compatibility. In this work, we incorporated diketopyrrolopyrrole (DPP), a well-established π-core for organic electronic applications, within the peptidic sequence. We embedded different numbers of thiophene rings (2 and 3) on both sides of the DPP to alter the length of the π-cores. We also varied the length of the N-alkyl side chains (methyl, butyl, hexyl) attached to the DPP core. These variations allowed us to explicitly study the effect of π-core and N-alkyl side-chain length on photophysical properties and morphology of the resulting nanomaterials. All of these molecules formed H-type aggregates in the assembled state. Longer π-cores have relatively red-shifted absorption maxima whereas the N-alkyl variation did not present significant photophysical changes.

show abstract

Mild synthesis and photophysical properties of symmetrically substituted diketopyrrolopyrrole derivatives

Cited by 16 publications

References 42 publications

Identification of Core Segment of Amyloidal Peptide Mediated by Chaperone Molecules by using Scanning Tunneling Microscopy

Identification of Core Segment of Amyloidal Peptide Mediated by Chaperone Molecules by using Scanning Tunneling Microscopy

Diketopyrrolopyrrole: brilliant red pigment dye-based fluorescent probes and their applications

Aqueous Self-Assembly of Peptide–Diketopyrrolopyrrole Conjugates with Variation of N-Alkyl Side Chain and π-Core Lengths

Contact Info

Product

Resources

About