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A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools

CHEMISTRY-A EUROPEAN JOURNAL (2023)

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Article Chemistry, Physical

Red-light driven photoisomerisation and supramolecular transformation of indigo amphiphiles in aqueous media

Ming-Hin Chau et al.

Summary: This study reports the newly designed red-light responsive N, N’-alkyl-aryl-substituted indigo amphiphiles, which exhibit excellent photoswitchability and photostability in organic media. When dissolved in aqueous media at pH 7, supramolecular nanostructures are constructed. Although the photoresponsiveness of these amphiphiles is slightly compromised, the co-solvent and co-assembly enable supramolecular transformations from vesicles to irregular aggregates in water. This work could provide a new strategy for the development of red-light controlled biomedical soft functional materials.

COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS (2023)

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Article Chemistry, Multidisciplinary

Red-light photoswitching of indigos in polymer thin films

Kim Kuntze et al.

Summary: By simple synthetic derivatisation, indigo dye can be converted into a red-light E-Z photoswitch, which exhibits negative photochromism and tuneable thermal isomerisation kinetics. This makes indigo derivatives highly attractive for materials and living systems applications. However, the translation of indigo photoswitching dynamics from solution to solid state, which is crucial for most applications, is not well understood. In this study, the photoswitching performance of six structurally distinct indigo derivatives in five polymers of varying rigidity is investigated. Three key strategies are identified to enable efficient photoswitching under red light: choosing a soft polymer matrix, creating free volume around the indigo molecules, and applying low dye loading to inhibit aggregation. Implementation of these strategies leads to isomerisation performance nearly identical to that in solution, paving the way for designing new red-light photochromic materials based on indigos.

CHEMICAL SCIENCE (2023)

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Article Chemistry, Multidisciplinary

A tunable synthesis of indigoids: targeting indirubin through temperature

James A. Shriver et al.

Summary: It has been demonstrated that selective synthesis of indirubins can be achieved by modulating reaction conditions and choosing appropriate indole compounds.

RSC ADVANCES (2022)

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Article Chemistry, Physical

Fine-Tuning the Thermal Relaxation Dynamics of Indigo-Based Photoswitches Using Selective Non-Covalent Interactions Without Chemical Modification

Zhen-Nan Shen et al.

Summary: Understanding the thermal relaxation dynamics is crucial for the application of photoswitches. Most strategies for regulating the thermal relaxation rates have focused on modifying the chemical structures. In this study, we demonstrate a complementary method for manipulating the thermal relaxation rate of indigo-based photoswitches without the need for chemical modification. By selectively stabilizing the parent structure of the metastable Z-isomer, we create a deactivated pathway that extends the thermal relaxation half-life. We also establish a quantitative kinetic model to show that controlling the strength of the selective stabilization allows for precise tuning of the thermal relaxation rates to achieve targeted values.

CHEMPHOTOCHEM (2022)

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Article Chemistry, Multidisciplinary

Mechanistic Insights into the Photoisomerization of N,N′-Disubstituted Indigos

Simon Budzak et al.

Summary: N,N'-disubstituted indigos are photoswitchable molecules that can be controlled by red-light. By tuning the N-substituents, the thermal stability of the molecules can be independently adjusted, while maintaining advantageous red-shifted absorption spectra. Photophysical and computational studies in solvents of different polarities revealed the photoisomerization mechanism of the molecules and the influence of the N-substituents on their switching properties. These mechanistic insights provide guidance for designing molecules with broader applications.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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Article Chemistry, Physical

Ultrafast Excited State Dynamics of Forward and Reverse trans-cis Photoisomerization of Red-Light-Absorbing Indigo Derivatives

Yu Kihara et al.

Summary: Femtosecond time-resolved transient absorption spectroscopy was used to investigate the excited state dynamics of red-light-absorbing indigo derivatives. The study found that both trans -> cis and trans <- cis photoisomerization have short excited state lifetimes, and are influenced by intramolecular charge transfer.

JOURNAL OF PHYSICAL CHEMISTRY B (2022)

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Article Materials Science, Multidisciplinary

Synthesis of asymmetric indolonaphthyridines with enhanced excited state charge-transfer character

Michael Purdy et al.

Summary: In this study, a new class of asymmetric indolonaphthyridines (IND) derived using a novel high yielding methodology was presented. The absorption properties and excited state charge-transfer character of these novel asymmetric INDs were compared with symmetric INDs. The results showed that the asymmetry of INDs increased the change in dipole moment and excited state charge-transfer character, which was attributed to the increased spatial separation between excited state electron and hole wavefunctions for the asymmetric INDs. The structure-property relationships introduced in this work provide invaluable design principles for the generation of high performance materials.

JOURNAL OF MATERIALS CHEMISTRY C (2022)

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Article Chemistry, Multidisciplinary

The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity

Patrick M. McCosker et al.

Summary: In this study, structurally diverse heterocycles were synthesized via cascade reactions of indigo with propargylic electrophiles, enabling chemical space exploration. It was found that the unsaturated propargyl moiety can act as an electrophile when aromatic terminal substitutions are made, competing with leaving group substitution to produce new outcomes. The products from these reactions were investigated for their absorption and fluorescence properties, revealing polarity dependent excited state relaxation pathways and highlighting these reactions as a rapid means to access diverse functional materials.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo

Christian Schnepel et al.

Summary: A biocatalytic approach was developed to selectively functionalize indigo derivatives, providing a modular platform for novel compounds with attractive spectral properties. This method not only improves yields but also allows for the synthesis of a small set of 6,6'-diarylindigo derivatives.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Organic

Synthesis of Bridged Indigos and Their Thermoisomerization and Photoisomerization Behaviors

Junya Kanda et al.

Summary: Bridged indigos, synthesized by bridging the two nitrogen atoms in the indigo structure with a carbon chain, exhibit intrinsic planar chirality. During thermo- and photoisomerization, the absence of (Z)-indigo and the presence of racemization can be attributed to the low activation energy of inversion and the significant energy difference between the ground states of (E)-indigo and (Z)-indigo.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Applied

Novel functionalized indigo derivatives for organic electronics

Irina V. Klimovich et al.

Summary: A series of novel indigo derivatives were synthesized and investigated as semiconductor materials in organic field-effect transistors, with different structures showing significant impact on charge transport properties. The results of this study will be important for the rational design of a new generation of indigo-based semiconductors.

DYES AND PIGMENTS (2021)

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Article Chemistry, Physical

Red-Purple Photochromic Indigos from Green Chemistry: Mono-tBOC or Di-tBOC N-Substituted Indigos Displaying Excited State Proton Transfer or Photoisomerization

Daniela Pinheiro et al.

Summary: This study investigates the characteristics of ESPT in indigo, the properties of different substitutions in solvents, and the pathways of excited-state deactivation. The photophysical properties and molecular structural features of indigo derivatives are discussed in relation to trans-cis photoisomerization and ESPT.

JOURNAL OF PHYSICAL CHEMISTRY B (2021)

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Article Chemistry, Organic

Stabilizing Indigo Z-Isomer through Intramolecular Associations of Redox-Active Appendages

Line Brolos et al.

Summary: In this study, the manipulation of the photostationary state was achieved by tethering two redox-active units to a photoswitchable molecule, resulting in enhanced stability of the Z-isomer through the formation of strong, intramolecular pi-dimers between the oxidized subunits. This stabilization is crucial for the applicability of photochromic systems in various fields.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Environment-friendly nanocellulose-indigo dyeing of textiles

Smriti Rai et al.

Summary: The environmentally sound indigo-dyeing technology utilizes nanocellulosic materials to significantly reduce water consumption and eliminate the use of toxic chemicals, achieving over 90% dye fixation compared to conventional methods. The one-step process for achieving lighter or darker shades simplifies the dyeing process and results in a more efficient and effective outcome.

GREEN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Deep in blue with green chemistry: influence of solvent and chain length on the behaviour of N- and N,N′- alkyl indigo derivatives

Daniela Pinheiro et al.

Summary: A series of indigo derivatives were synthesized using green chemistry procedures, with the alkyl chain length and solvent type found to influence the spectral and photophysical properties of the compounds, including the excited state proton transfer process. Time-resolved experiments indicated that different solvents led to variations in the decay behavior of the compounds, highlighting the importance of solvent effects on the photochemical behavior of the molecules.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Applied

Indigo chromophores and pigments: Structure and dynamics

V. V. Volkov et al.

DYES AND PIGMENTS (2020)

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Review Chemistry, Multidisciplinary

Enlightening Materials with Photoswitches

Alexis Goulet-Hanssens et al.

ADVANCED MATERIALS (2020)

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Review Biotechnology & Applied Microbiology

An overview of microbial indigo-forming enzymes

Andrea N. Fabara et al.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2020)

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Article Chemistry, Applied

I2/NaH/DMF as oxidant trio for the synthesis of tryptanthrin from indigo or isatin

Pedro Brandao et al.

DYES AND PIGMENTS (2020)

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Review Chemistry, Inorganic & Nuclear

Metal Complexes of Indigo and of Some Related Ligands

Wolfgang Beck et al.

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE (2020)

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Review Plant Sciences

Isatis tinctoria L. (Woad): A Review of Its Botany, Ethnobotanical Uses, Phytochemistry, Biological Activities, and Biotechnological Studies

Jasmine Speranza et al.

PLANTS-BASEL (2020)

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Article Chemistry, Applied

Photoresponsive N,N′-disubstituted indigo derivatives

Daniela C. Nobre et al.

DYES AND PIGMENTS (2020)

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Article Chemistry, Physical

Solvent Mediated Excited State Proton Transfer in Indigo Carmine

Partha Pratim Roy et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2020)

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Article Chemistry, Organic

Crystal structure and homopolar dihydrogen interactions in propano-bridged indigo

Bidyut Das et al.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY (2020)

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Article Biochemistry & Molecular Biology

Synthesis and Characterization of New Organic Dyes Containing the Indigo Core

Daniele Franchi et al.

MOLECULES (2020)

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Article Chemistry, Organic

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

Hyejin Hong et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

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Article Chemistry, Applied

Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization

Tao Jia et al.

DYES AND PIGMENTS (2019)

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Article Chemistry, Physical

Ultrafast Excited-State Intermolecular Proton Transfer in Indigo Oligomer

Xuemei He et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2019)

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Article Chemistry, Multidisciplinary

Nitrogen Bridged Diazocines: Photochromes Switching within the Near-Infrared Region with High Quantum Yields in Organic Solvents and in Water

Pascal Lentes et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Review Chemistry, Inorganic & Nuclear

The coordination potential of indigo, anthraquinone and related redox-active dyes

Wolfgang Kaim et al.

COORDINATION CHEMISTRY REVIEWS (2019)

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Article Chemistry, Organic

Desymmetrization Reactions of Indigo with Grignard Reagents for the Synthesis of Selective Antiplasmodial [1H,3′H]-3-Aryl-2,2′-diindol-3′-ones

Nicholas M. Butler et al.

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Exploiting Excited-State Aromaticity To Design Highly Stable Singlet Fission Materials

Kealan J. Fallon et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

High-Performance Ambipolar Polymers Based on Electron-Withdrawing Group Substituted Bay-Annulated Indigo

Jie Yang et al.

ADVANCED FUNCTIONAL MATERIALS (2019)

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Article Chemistry, Physical

Towards More Effective, Reversible pH Control by Visible Light Alone: A Thioindigo Photoswitch Undergoing a Strong pKa Modulation by Isomer-Specific Hydrogen Bonding

Benjamin Koeppe et al.

CHEMPHOTOCHEM (2019)

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Article Chemistry, Multidisciplinary

Design and synthesis of stable indigo polymer semiconductors for organic field-effect transistors with high fluoride sensitivity and selectivity

Jenner H. L. Ngai et al.

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Review Chemistry, Multidisciplinary

Indigoid Photoswitches: Visible Light Responsive Molecular Tools

Christian Petermayer et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

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Solvent dependent trans -> cis photoisomerization of N, N '-diacetylindigo studied by femtosecond time-resolved transient absorption spectroscopy

Hirofumi Nakagawa et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2018)

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Maxim E. Zhidkov et al.

TETRAHEDRON LETTERS (2018)

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Synthesis and peripheral substituent effects of bay-annulated indigo derivatives

Taniyuki Furuyama et al.

TETRAHEDRON LETTERS (2018)

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Cascade reactions of indigo with oxiranes and aziridines: efficient access to dihydropyrazinodiindoles and spiro-oxazocinodiindoles

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Biodegradation and Biotransformation of Indole: Advances and Perspectives

Qiao Ma et al.

FRONTIERS IN MICROBIOLOGY (2018)

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Photoisomerization of Mono-Arylated Indigo and Water-Induced Acceleration of Thermal cis-to-trans Isomerization

Ludwig A. Huber et al.

CHEMPHOTOCHEM (2018)

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Alternating donor-acceptor indigo-cyclopentadithiophene copolymers: competition between excited state conformational relaxation, energy transfer and excited state proton transfer

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CHEMICAL REVIEWS (2017)

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Excited-State Proton Transfer in Indigo

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JOURNAL OF PHYSICAL CHEMISTRY B (2017)

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Article Chemistry, Multidisciplinary

N,N'-Disubstituted Indigos as Readily Available Red-Light Photoswitches with Tunable Thermal Half-Lives

Chung-Yang Huang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Time-Resolved Spectroscopy of Indigo and of a Maya Blue Simulant

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Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor-Acceptor Constructs

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Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

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Protoisomerization of indigo di- and monoimines

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Planar and distorted indigo as the core motif in novel chromophoric liquid crystals

Jan H. Porada et al.

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Regioisomeric control of charge transport polarity for indigo-based polymers

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Photostability of 4,4′-Dihydroxythioindigo, a Mimetic of Indigo

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Biomimetic oxidation of indole by Mn(III)porphyrins

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Photoinduced Pigmentation Using Base-reactive Indigo Precursors in a Polymer Film

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New Form of an Old Natural Dye: Bay-Annulated Indigo (BAI) as an Excellent Electron Accepting Unit for High Performance Organic Semiconductors

Bo He et al.

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Chang Guo et al.

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Air-stable organic semiconductors based on 6,6′-dithienylindigo and polymers thereof

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25th Anniversary Article: Progress in Chemistry and Applications of Functional Indigos for Organic Electronics

Eric Daniel Glowacki et al.

ADVANCED MATERIALS (2013)

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Observation of Dynamic Behavior of Self-Assembled N-Icosyl-Substituted Indigo by STM

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Patterned Fluorescence Images with Indigo Precursors in Polymer Film

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A facile protection-deprotection route for obtaining indigo pigments as thin films and their applications in organic bulk heterojunctions

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Rapid Cascade Synthesis of Poly-Heterocyclic Architectures from Indigo

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A theoretical study of the photochemistry of indigo in its neutral and dianionic (leucoindigo) forms

Miquel Moreno et al.

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Light-Controlled Tools

Clara Brieke et al.

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Eric Daniel Glowacki et al.

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Molecular Description of Indigo Oxidation Mechanisms Initiated by OH and OOH Radicals

Cristina Iuga et al.

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Excited-State Isomerization of Leuco Indigo

R. Rondao et al.

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Nonadiabatic dynamics of a truncated indigo model

Ganglong Cui et al.

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Excited state characterization of a polymeric indigo

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PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2012)

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Article Chemistry, Physical

On the intrinsic photophysics of indigo: a time-resolved photoelectron spectroscopy study of the indigo carmine dianion

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PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2012)

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Review Chemistry, Inorganic & Nuclear

The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions

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Indigo carmine: Understanding a problematic blue dye

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Review Chemistry, Multidisciplinary

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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Transition State in a Prevented Proton Transfer Observed in Real Time

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BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2011)

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Article Chemistry, Multidisciplinary

Development of a Practical One-Pot Synthesis of Indigo from Indole

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BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2011)

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Article Chemistry, Multidisciplinary

Pd-Catalyzed Direct and Selective C-H Functionalization: C3-Acetoxylation of Indoles

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CHEMISTRY-A EUROPEAN JOURNAL (2011)

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Article Chemistry, Inorganic & Nuclear

Redox-Active Bridging Ligands Based on Indigo Diimine (Nindigo) Derivatives

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INORGANIC CHEMISTRY (2011)

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Article Chemistry, Physical

Theoretical and experimental investigation on the spectroscopic properties of indigo dye

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JOURNAL OF MOLECULAR STRUCTURE (2011)

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Palladium-Catalyzed Direct and Regioselective C-H Bond Functionalization/Oxidative Acetoxylation of Indoles

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JOURNAL OF ORGANIC CHEMISTRY (2011)

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Article Chemistry, Physical

Indigo stability: an ab initio study

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MOLECULAR SIMULATION (2011)

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Molecular mechanisms of the photostability of indigo

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PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2011)

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Photoswitches: From Molecules to Materials

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Nindigo'': synthesis, coordination chemistry, and properties of indigo diimines as a new class of functional bridging ligands

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CHEMICAL COMMUNICATIONS (2010)

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Article Chemistry, Physical

Kinetic isotope effect on the proton-transfer in indigo carmine

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CHEMICAL PHYSICS LETTERS (2010)

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Article Chemistry, Physical

Characterization of the Excited States of Indigo Derivatives in their Reduced Forms

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CHEMPHYSCHEM (2010)

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Review Biochemistry & Molecular Biology

Preparation of Tyrian Purple (6,6′-Dibromoindigo): Past and Present

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MOLECULES (2010)

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Article Chemistry, Organic

Bromamine-B/PdCl2 is an Efficient System for the Synthesis of Anthranilic Acids from Indoles and Indigos

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SYNTHETIC COMMUNICATIONS (2010)

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Article Chemistry, Multidisciplinary

Why is Indigo Photostable over Extremely Long Periods?

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CHEMISTRY LETTERS (2009)

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Review Chemistry, Applied

The development of indigo reduction methods and pre-reduced indigo products

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COLORATION TECHNOLOGY (2009)

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Polymeric Colorants: Statistical Copolymers of Indigo Building Blocks with Defined Structures

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HELVETICA CHIMICA ACTA (2009)

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Highly Efficient Reversible Z-E Photoisomerization of a Bridged Azobenzene with Visible Light through Resolved S1(nπ*) Absorption Bands

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

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Article Chemistry, Organic

Novel spiro and fused heterocycles from the allylation of indigo

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TETRAHEDRON LETTERS (2009)

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Article Biochemistry & Molecular Biology

A photochemical study on the blue dye indigo: from solution to ancient Andean textiles

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Why is indigo blue?

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BIOTECHNIC & HISTOCHEMISTRY (2007)

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Bibliography Biotechnology & Applied Microbiology

Indigo: an annotated bibliography

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BIOTECHNIC & HISTOCHEMISTRY (2007)

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Article Chemistry, Physical

Photophysics of an indigo derivative (keto and leuco structures) with singular properties

J. Seixas de Melo et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2006)

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Article Chemistry, Physical

Spectral and photophysical studies of substituted indigo derivatives in their keto forms

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CHEMPHYSCHEM (2006)

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Article Chemistry, Organic

Synthesis of the first deprotected indigo N-glycosides (blue sugars) by reductive glycosylation of dehydroindigo

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TETRAHEDRON LETTERS (2006)

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Article Chemistry, Physical

Substitution and chemical environment effects on the absorption spectrum of indigo

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JOURNAL OF CHEMICAL PHYSICS (2006)

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First synthesis of N-indigoglycosides -: Analogues of cancerostatic akashines

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SYNTHESIS-STUTTGART (2005)

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Article Chemistry, Physical

Photophysical and spectroscopic studies of Indigo derivatives in their keto and leuco forms

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JOURNAL OF PHYSICAL CHEMISTRY A (2004)

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Article Chemistry, Applied

A facile synthesis of 6,6′- and 5,5′-dihalogenoindigos

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DYES AND PIGMENTS (2004)

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Analysis of the conversion of indigo into indigo carmine dye using SERRS

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CHEMICAL COMMUNICATIONS (2004)

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Photoacid-catalysed pigmentation of dyestuff precursors enhanced by acid amplifiers in polymer films

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JOURNAL OF MATERIALS CHEMISTRY (2004)

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Article Chemistry, Physical

The effect of hydrogen-bonding on the ultrafast electronic deactivation dynamics of indigo carmine

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PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2004)

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Review Chemistry, Multidisciplinary

The natural constituents of historical textile dyes

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CHEMICAL SOCIETY REVIEWS (2004)

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Article Chemistry, Multidisciplinary

Highly soluble and green indigo dyes: 4,4 ',7,7 '-tetraalkoxy-5,5 '-diaminoindigotins

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HELVETICA CHIMICA ACTA (2003)

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Article Biochemistry & Molecular Biology

Identification of an indigo precursor from leaves of Isatis tinctoria (Woad)

T Maugard et al.

PHYTOCHEMISTRY (2001)

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Review Biochemistry & Molecular Biology

Tyrian purple:: 6,6′-dibromoindigo and related compounds

CJ Cooksey

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A facile synthesis of Tyrian purple based on a biosynthetic pathway

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Organic photochromism

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PURE AND APPLIED CHEMISTRY (2001)

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An improved synthetic procedure for 6,6 '-dibromoindigo (tyrian purple)

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SYNTHETIC COMMUNICATIONS (2001)

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