Azulene as an ingredient for visible-light- and stimuli-responsive photoswitches

2021 ◽  
Author(s):  
Andrey G. Lvov ◽  
Aleksei Bredihhin
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Unique Combination ◽  
Stimuli Responsive

The azulene molecule features an unique combination of optical, luminescent, and stimuli-responsive properties. This makes the azulene motif a promising functional group to be introduced in photoswitches. Recent challenges in...

scholarly journals Thermo- and Photoresponsive Behaviors of Dual-Stimuli-Responsive Organogels Consisting of Homopolymers of Coumarin-Containing Methacrylate

Polymers ◽  
2021 ◽  
Vol 13 (3) ◽  
pp. 329
Author(s):  
Seidai Okada ◽  
Eriko Sato
Keyword(s):  
Functional Group ◽  
Solution Temperature ◽  
Stimuli Responsive ◽  
Critical Solution Temperature ◽  
Equilibrium Degree ◽  
Stimuli Responsive Polymers ◽  
Responsive Polymers ◽  
Dual Functional ◽  
Wide Range ◽  
Increasing Temperature

Coumarin-containing vinyl homopolymers, such as poly(7-methacryloyloxycoumarin) (P1a) and poly(7-(2′-methacryloyloxyethoxy)coumarin) (P1b), show a lower critical solution temperature (LCST) in chloroform, which can be controlled by the [2 + 2] photochemical cycloaddition of the coumarin moiety, and they are recognized as monofunctional dual-stimuli-responsive polymers. A single functional group of monofunctional dual-stimuli-responsive polymers responds to dual stimuli and can be introduced more uniformly and densely than those of dual-functional dual-stimuli-responsive polymers. In this study, considering a wide range of applications, organogels consisting of P1a and P1b, i.e., P1a-gel and P1b-gel, respectively, were synthesized, and their thermo- and photoresponsive behaviors in chloroform were investigated in detail. P1a-gel and P1b-gel in a swollen state (transparent) exhibited phase separation (turbid) through a temperature jump and reached a shrunken state (transparent), i.e., an equilibrium state, over time. Moreover, the equilibrium degree of swelling decreased non-linearly with increasing temperature. Furthermore, different thermoresponsive sites were photopatterned on the organogel through the photodimerization of the coumarin unit. The organogels consisting of homopolymers of coumarin-containing methacrylate exhibited unique thermo- and photoresponsivities and behaved as monofunctional dual-stimuli-responsive organogels.

Acetylation of Alcohols and Amines under Visible Light Irradiation: Diacetyl as an Acylation Reagent and Photosensitizer

2021 ◽  
Author(s):  
Pengcheng Lian ◽  
Ruyi Li ◽  
Xiao Wan ◽  
Zixin Xiang ◽  
Hang Liu ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Functional Group ◽  
Environmentally Friendly ◽  
Light Irradiation ◽  
Environmentally Friendly Process

This work developed an unprecedented strategy for the acetylation of alcohols and amines using diacetyl as both an acylation reagent and photosensitizer. This environmentally friendly process exhibits excellent functional group...

Bromotrifluoromethane: A Useful Reagent for Hydrotrifluoromethylation of Alkenes and Alkynes

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1028-1032 ◽  
Author(s):  
Xing Zheng ◽  
Xingang Zhang ◽  
Yu-Yan Ren
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Functional Group ◽  
Mild Conditions ◽  
Industrial Material ◽  
Reaction Proceeds

Bromotrifluoromethane (CF3Br) is a simple, inexpensive and abundant industrial material employed as a trifluoromethylating reagent. However, only limited strategies using CF3Br as a fluorine source are reported. Herein, we describe a visible-light-induced hydrotrifluoromethylation of alkenes and alkynes with CF3Br. The reaction proceeds under mild conditions with good functional group tolerance, providing a new route for the application of BrCF3 in organic synthesis.

Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

2020 ◽  
Vol 18 (23) ◽  
pp. 4390-4394
Author(s):  
Jia-Hui Zhao ◽  
Zhao-Zhao Zhou ◽  
Yue Zhang ◽  
Xuan Su ◽  
Xi-Meng Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Palladium Complex ◽  
Alkyl Halides ◽  
Palladium Catalyzed ◽  
High Yields

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility.

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

A mild, general, and metal-free method for site-specific deuteration induced by visible light using D2O as the source of deuterium atoms

2020 ◽  
Vol 22 (3) ◽  
pp. 669-672 ◽  
Author(s):  
Shuai Shi ◽  
Ruining Li ◽  
Liangming Rao ◽  
Zhankui Sun
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Site Specific ◽  
Metal Free ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Radical Approach

Visible light induced desulfurization–deuteration method was developed using D2O as the source of deuterium atoms. This radical approach features mild conditions, broad substrate scope, highly efficient D-incorporation and excellent functional group compatibility.

Visible-light-induced anti-Markovnikov hydrosulfonation of styrene derivatives

2020 ◽  
Vol 7 (15) ◽  
pp. 2069-2074 ◽  
Author(s):  
Yinan Zheng ◽  
Ying You ◽  
Qianqian Shen ◽  
Junjie Zhang ◽  
Le Liu ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Styrene Derivatives

A visible-light-induced anti-Morkovnikov hydrosulfonation reaction of styrene derivatives with sodium sulfinates has been developed, featuring mild reaction conditions, good functional-group tolerance, good yields and high regioselectivity.

scholarly journals Direct sulfonylation of anilines mediated by visible light

2018 ◽  
Vol 9 (3) ◽  
pp. 629-633 ◽  
Author(s):  
Tarn C. Johnson ◽  
Bryony L. Elbert ◽  
Alistair J. M. Farley ◽  
Timothy W. Gorman ◽  
Christophe Genicot ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Visible Light Photocatalysis ◽  
Reaction Conditions

Visible light photocatalysis allows the introduction of the sulfone functional group to anilines under mild reaction conditions, without the need for pre-functionalization.

scholarly journals Tyrosine and Drug-like Late-stage Benzylic Functionalization via Photoredox Catalysis

2020 ◽  
Author(s):  
Tobias Brandhofer ◽  
Volker Derdau ◽  
María Mendez ◽  
Christoph Pöverlein ◽  
Olga Garcia Mancheno
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Functional Group ◽  
Reaction Conditions ◽  
Site Selectivity ◽  
Wide Range ◽  
High Yields ◽  
Therapeutic Compounds

Abstract Visible light mediated late-stage functionalization is a rising field in synthetic and medicinal chemistry, allowing the fast and diversified modification of valuable, potentially therapeutic compounds such as peptides. However, there are relatively few mild methodologies for the C(sp3)-H functionalization of complex peptides. Herein, we report a visible light mediated photocatalytic protocol for the benzylic C-H modification of tyrosine and related C-H bonds. The embraced radical-cation/deprotonation strategy enables an incorporation of a wide range of valuable functional groups in high yields and chemoselectivity. The mild reaction conditions, site-selectivity and high functional group tolerance was highlighted by the functionalization of complex peptides, drugs and natural products, providing a promising synthetic platform in medicinal chemistry.

scholarly journals Catalytic Asymmetric Allylation of Aldehydes with Alkenes Mediated by Organophotoredox and Chiral Chromium Hybrid Catalysis

2018 ◽  
Author(s):  
Harunobu Mitsunuma ◽  
Shun Tanabe ◽  
Hiromu Fuse ◽  
Kei Ohkubo ◽  
Motomu Kanai
Keyword(s):  
Visible Light ◽  
Hybrid System ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Functional Group ◽  
Light Irradiation ◽  
Asymmetric Allylation ◽  
Complex Catalyst ◽  
Homoallylic Alcohols ◽  
Catalytic Asymmetric

A hybrid system accomplishing cooperativity between an organophotoredox acridinium catalyst and a chiral chromium<br>complex catalyst was developed, enabling the unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for the asymmetric allylation of aldehydes. The reaction proceeded under visible light irradiation at room temperature and with high functional group tolerance, affording the corresponding homoallylic alcohols with up to >20/1 diastereomeric ratio and 99% ee. The addition of Mg(ClO4)2 elicited profound enhancement of both reactivity and enantioselectivity.

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