The author greatly acknowledges the financial support from the Spanish Ministry of Economy and Competitiveness (CTQ2014-52687-C3-1-P project) and Marie Sklodowska Curie Initial Training Networks (FP7-PEOPLE-2013-ITN, BIBAFOODS project). The author also acknowledges support from Generalitat de Catalunya (2014SGR1655 and TECCIT15-1-0009) and Centro de Investigacion Biomedica en Red de Bioingenieria, Biomateriales y Nanomedicina (CIBER-BBN).

Current Opinion in Colloid and Interface Science

Temperature-responsive ionic liquids (ILs), their fundanmental behaviors, and catalytic applications were introduced, especially the concepts of upper critical solution temperature (UCST) and lower critical solution temperature (LCST). It is described that, during a catalytic reaction, they form a homogeneous mixture with the reactants and products at reaction temperature but separate from them afterward at ambient conditions. It is shown that this behavior offers an effective alternative approach to overcome gas/liquid–solid interface mass transfer limitations in many catalytic transformations. It should be noted that IL-based thermomorphic systems are rarely elaborated until now, especially in the field of catalytic applications. The aim of this article is to provide a comprehensive review about thermomorphic mixtures of an IL with H2O and/or organic compounds. Special focus is laid on their temperature dependence concerning UCST and LCST behavior, including systems with conventional ILs, metal-containi...

Temperature-Responsive Ionic Liquids: Fundamental Behaviors and Catalytic Applications

Water-in-water (W/W) emulsions are colloidal dispersions of an aqueous solution into another aqueous phase. Such dispersions can be formed in mixtures of at least two hydrophilic macromolecules, which are thermodynamically incompatible in solution, generating two immiscible aqueous phases. W/W emulsions are much less known than conventional oil-in-water or water-in-oil emulsions, despite the fact that phase separation in aqueous mixtures is highly common. The thermodynamics and the phase behavior of segregative phase separation in mixtures of hydrophilic polymers have focused a great attention, with many excellent scientific reports in the literature. However, the kinetic stability of water-in-water emulsions is generally difficult to control, since amphiphilic molecules do not adsorb on water-water interfaces. Consequently, surfactants are not good stabilizers for W/W emulsions, and until recently, only a limited number of scientific studies have dealt with the formation and stabilization of emulsions in aqueous two-phase systems. Recent advances and successful results in the stabilization of these emulsions, by alternative mechanisms, have triggered a renewed interest. Nowadays, fast progress is being made in formation and stabilization methods, and new knowledge is rapidly acquired, opening a wide range of novel possibilities for practical applications. Interestingly, highly stable water-in-water emulsions can be formulated using fully biocompatible and edible components, and consequently, these emulsions can be used in food formulations, among many other interesting applications. This review describes the general background of research in the field, and focuses on recent scientific advances, including phase behavior, formation, stability and kinetic aspects, as well as applications such as formation of microgels, encapsulation and drug delivery.

Water-in-water (W/W) emulsions

Living cells have evolved over billions of years to develop structural and functional complexity with numerous intracellular compartments that are formed due to liquid-liquid phase separation (LLPS). Discovery of the amazing and vital roles of cells in life has sparked tremendous efforts to investigate and replicate the intracellular LLPS. Among them, all-aqueous emulsions are a minimalistic liquid model that recapitulates the structural and functional features of membraneless organelles and protocells. Here, an emerging all-aqueous microfluidic technology derived from micrometer-scaled manipulation of LLPS is presented; the technology enables the state-of-art design of advanced biomaterials with exquisite structural proficiency and diversified biological functions. Moreover, a variety of emerging biomedical applications, including encapsulation and delivery of bioactive gradients, fabrication of artificial membraneless organelles, as well as printing and assembly of predesigned cell patterns and living tissues, are inspired by their cellular counterparts. Finally, the challenges and perspectives for further advancing the cell-inspired all-aqueous microfluidics toward a more powerful and versatile platform are discussed, particularly regarding new opportunities in multidisciplinary fundamental research and biomedical applications.

https://onlinelibrary.wiley.com/doi/epdf/10.1002/advs.201903359

Cell-Inspired All-Aqueous Microfluidics: From Intracellular Liquid–Liquid Phase Separation toward Advanced Biomaterials

Readily accessible and shelf-stable 1,2,3-triazole and its analogues such as pyridotriazole, triazoloindole, benzotriazole, and thiadiazole exist in equilibrium with their ring-opened isomers, viz., diazo compounds. These ring-opened isomers could be trapped by various metal catalysts (e.g., Rh, Pd, Cu, Co, Ag, etc.) to generate the corresponding metal carbenoids with extrusion of nitrogen. As a consequence, these unique N-heterocycles facilitate access to a realm of N-containing complex structural motifs of biological importance through denitrogenative transformations such as transannulations, insertions, ylide formation, and rearrangements by trapping of the metal carbenoids with a diverse range of coupling partners (e.g., alkenes, alkynes, nitriles, carbo/heterocycles, X-H/C-X bonds, etc.). Hence, suitably substituted triazole derivatives have emerged as efficient surrogates of diazo compounds for the generation of reactive metal carbenoids during the past decades. In this comprehensive review, we aim to discuss in detail the remarkable advancement in their synthesis and synthetic applications.

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds.

Metal-free syntheses of N-functionalized and NH-1,2,3-triazoles: an update on recent developments.

The development of metal-free syntheses toward 1,2,3-triazoles has been a burgeoning research area throughout the past decade. Despite the numerous advances, the scarceness of methods for the preparation of 1,5-disubstituted 1,2,3-triazoles from readily available substrates remained a challenge that was addressed by our group in 2016. A metal-free three-component reaction, which we have dubbed the triazolization reaction, was established for the rapid synthesis of 1,5-disubstituted, fully functionalized and NH-1,2,3-triazoles. This novel approach stands out because it utilizes widely available starting materials, namely primary amines and enolizable ketones. Furthermore, the broad substrate scope is a major advantage, and was further expanded by the number of modified protocols that have been reported. Triazolization products have successfully found utility as intermediates in various synthetic transformations, and were the subject of a few interesting biological activity studies.

Triazolization of Enolizable Ketones with Primary Amines: A General Strategy toward Multifunctional 1,2,3-Triazoles.

In recent years, several organocatalytic/metal-free synthetic pathways towards 1,2,3-triazoles have been reported. One of them is a general metal-free route towards the synthesis of 1,5-di- or fully-substituted 1,2,3-triazoles, designed by our group and named the ‘triazolization’ reaction of ketones. Limitations of this route were encountered in reactions with more activated ketones, where the corresponding 1-(4-nitrophenyl)-1,2,3-triazole was found back as the major product. Interestingly, three different triazoles are formed when 1,3-diphenylacetone is used as the ketone. In the present work, 1,3-diphenylacetone was used as a model substrate to investigate the chemoselectivity of our metal-free route under different reaction circumstances. This led to the conclusion that the formation of the desired 1,2,3-triazole is favored in apolar solvents, at high temperatures, and in the presence of acetic acid. By using one equivalent of acetic acid, previously inaccessible fully decorated 1,2,3-triazoles can be synthesized from simple α-arylketones in moderate to high yields.

Chemoselectivity in the Synthesis of 1,2,3-Triazoles from Enolizable Ketones, Primary Alkylamines, and 4-Nitrophenyl Azide

The research field of 1,2,4-triazoles has been covered from 2007 until June 2019. In this period, a vast number of publications have appeared on the topic. An attempt was made to review the most important publications on the properties ( 2 Theoretical methods , 3 Experimental structural methods , 4 Thermodynamic aspects ), reactivity ( 5 Reactivity of fully conjugated rings , 6 Reactivity of non-conjugated rings , 7 Reactivity of substituents ), ring synthesis ( 8 Ring synthesis from acyclic compounds , 9 Ring synthesis by transformation of another ring ), and various applications ( Section 10 ) of this heterocycle. For a comprehensive view of the field, it is recommended to read this article together with the earlier articles published in CHECI (1984), CHEC-II (1996) and CHEC-III (2008).

1,2,4-Triazoles

The 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies involving click−cyclization−aromatization domino reactions, gold-catalyzed cyclization of propargyl triazoles or triazolization of acetophenones. As a result, TAPs with diverse substitution patterns were obtained, showing varying fluorescence properties. Based on these properties, several TAPs have been selected and studied as fluorescent imaging probes in living cells and as sensors. This mini review provides an overview of the research on the bicyclic TAPs and does not comment on the literature about benzo or otherwise fused systems. The synthetic methodologies for the preparation of TAPs, the substituent effects on the fluorescence properties, and the behavior of the TAP core as an element of biological imaging probes and sensors are discussed.

Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes

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