Discovery and properties of a new indigoid structure type based on dimeric <i>cis</i>-indigos

Hong, Hyejin; Conover, Cassidy M.; Hofsommer, Dillon T.; Sanz, Corey A.; Hicks, Robin G.

doi:10.1039/d0ob01368d

Cited by 2 publications

(3 citation statements)

References 124 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indigo as an ancient natural dye is extracted from tropical plants, woad ( Isatis tinctoria ), and true indigo ( Indigofera tinctoria ) [ 99 , 100 ], and it is a remarkably stable blue dye and has a long history of use in textiles. The bis(indole) indigotin is responsible for the blue color of indigo-based dyes [ 101 ] and a new class of indigoids has been discovered [ 102 ]. FD&C blue no.…”

Section: Resultsmentioning

confidence: 99%

Insight into the Progress on Natural Dyes: Sources, Structural Features, Health Effects, Challenges, and Potential

Wang

Zhou

et al. 2022

Molecules

View full text Add to dashboard Cite

(1) Background: Dyes play an important role in food, medicine, textile, and other industries, which make human life more colorful. With the increasing demand for food safety, the development of natural dyes becomes more and more attractive. (2) Methods: The literature was searched using the electronic databases PubMed, Web of Science, and SciFinder and this scoping review was carried out following Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA). (3) Results: 248 articles were included in this review. This review summarizes the research progress on natural dyes in the last ten years. According to structural features, natural dyes mainly include carotenoids, polyphenols, porphyrins, and alkaloids, and some of the newest dyes are summarized. Some pharmacological activities of carotenoids, anthocyanin, curcumin, and betalains in the last 10 years are summarized, and the biological effects of dyes regarding illumination conditions. The disadvantages of natural dyes, including sources, cost, stability, and poor bioavailability, limit their application. Here, some feasible strategies (potential resources, biotechnology, new extraction and separation strategies, strategies for improving stability) are described, which will contribute to the development and utilization of natural dyes. (4) Conclusion: Natural dyes show health benefits and potential in food additives. However, it is necessary for natural dyes to pass toxicity tests and quality tests and receive many regulatory approvals before their final entry into the market as food colorants or as drugs.

show abstract

Section: Resultsmentioning

confidence: 99%

Insight into the Progress on Natural Dyes: Sources, Structural Features, Health Effects, Challenges, and Potential

Wang

Zhou

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

“…Other indigo N ‐alkylation reactions include an intriguing transformation reported by the groups of Pummerer and Scheibe, where they showed that dehydroindigo undergoes 1,2‐addition to olefin such as styrene and succinic anhydride to form Z ‐configured cyclic structures (Scheme 21). [60] Hicks and co‐workers also found similar reactions where an indigo molecule is added across the central double bond of another indigo in a cis‐fashion [61] …”

Section: Indigo Functionalizationmentioning

confidence: 93%

“…[60] Hicks and co-workers also found similar reactions where an indigo molecule is added across the central double bond of another indigo in a cis-fashion. [61] Another interesting class of molecules is N-indigoglycosides. In 2002, the Laatsch group reported the structural elucidation of 5,5'-dichloroindigo derivatives isolated from plants, and they termed these compounds akashins A, B, and C. [62] Hein, Langer, and co-workers later embarked on the synthetic studies and developed strategies for indigo N-glycosylations (Scheme 22).…”

Section: N-alkylationmentioning

confidence: 99%

A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools

Huang

Hecht

2023

Chemistry A European J

View full text Add to dashboard Cite

Indigo, one of the most ancient and abundant dyes in human history, has recently emerged as a potential functional motif due to its intriguing photochemical properties. This review aims to provide insights into both the preparation of these molecules and their utilization in molecular systems. First, the synthesis of the indigo core as well as available methods to derivatize indigo are described to outline synthetic strategies to build the desired molecular structures. Then, the photochemical behavior of indigos is discussed, with particular focus on E-Z photoisomerization and photoinduced electron transfer. Connections between the molecular structures and their photochemical properties are highlighted and serve as guiding principles for designing indigos to be applied as photoresponsive tools.

show abstract

Discovery and properties of a new indigoid structure type based on dimeric cis-indigos

Abstract: Reactions of indigo with quinones in the presence of NaH leads to products containing two indigo subunits; one indigo is in a cis configuration and fused via its indole nitrogen atoms to a second indigo at the central C–C bond of the latter.

Cited by 2 publications

References 124 publications

Insight into the Progress on Natural Dyes: Sources, Structural Features, Health Effects, Challenges, and Potential

Insight into the Progress on Natural Dyes: Sources, Structural Features, Health Effects, Challenges, and Potential

A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools

Contact Info

Product

Resources

About