Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

SN2 Reaction: Transition State

S_N2 Reaction: Transition State

An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...

SN2 Reaction: Stereochemistry

S_N2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...

Directing and Steric Effects in Disubstituted Benzene Derivatives

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...

Directing Effect of Substituents: meta-Directing Groups

Directing Effect of Substituents: meta-Directing Groups

Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...

Predicting Products: SN1 vs. SN2

Predicting Products: S_N1 vs. S_N2

Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the substrate simultaneously as the leaving group departs, in SN1 reactions, the substrate first dissociates to give the carbocation intermediate. Various factors such as the structure of the substrate, the strength of the nucleophile, and the nature of the solvent promote one mechanism over the other.
With increased substitution on the alkyl halide,...

SN1 Reaction: Kinetics

S_N1 Reaction: Kinetics

In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Utilizing Light to Control Glycopolymer-DC-SIGN Interactions via Molecular Motors.

Journal of the American Chemical Society·2026

Same author

Light-Driven Dual Rotary Molecular Motors and Beyond.

Accounts of chemical research·2026

Same author

Benzene at 200: from a simple ring to a universe of fused aromatic carbon.

Chemical science·2026

Same author

Temperature- and Light-Regulated Liquid Crystal Smart Window for Dynamic Control of Daylight and Solar Heat in All-Weather Conditions.

Angewandte Chemie (International ed. in English)·2026

Same author

Engineering Highly Photoefficient and Function-Tunable Molecular Rotary Motors toward Sunlight Responsiveness.

Journal of the American Chemical Society·2026

Same author

Fully Reversible Photocontrol over DNA Intercalation with Visible Light.

Journal of the American Chemical Society·2026

Search research articles

Related Experiment Video

Updated: Sep 13, 2025

Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks

Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks

Published on: November 25, 2015

Substituent effects in a six-state molecular switch.

Rachael Hannah¹, Kirsten M van der Geest¹, Shahrzad Shafei¹

¹Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 3, 9747 AG Groningen, The Netherlands.

Physical Chemistry Chemical Physics : PCCP

|July 31, 2025

Summary

This summary is machine-generated.

This study introduces novel indolinooxazolidine molecular switches. These multistate photoswitches offer six distinct states through photo- and stereo-isomerism, advancing molecular device capabilities.

More Related Videos

Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch

Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch

Published on: February 7, 2022

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Published on: July 19, 2019

Related Experiment Videos

Last Updated: Sep 13, 2025

Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks

Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks

Published on: November 25, 2015

Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch

Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch

Published on: February 7, 2022

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Published on: July 19, 2019

Area of Science:

Organic Chemistry
Materials Science
Supramolecular Chemistry

Background:

Photoswitches are crucial for molecular devices, enabling state changes via light.
Most photoswitches are binary, limiting their application in complex architectures.
Multistate switches offer enhanced functionality for advanced molecular systems.

Purpose of the Study:

To synthesize and characterize a series of indolinooxazolidine molecular switches.
To investigate the influence of electronic structure and substituents on switching behavior.
To explore the potential for multistate switching using photo- and stereo-isomerism.

Main Methods:

Synthesis of four indolinooxazolidine derivatives with varied electronic structures.
Examination of photoisomerization and acidochromic switching in different solvents.
Analysis of the impact of electron-withdrawing groups and oligoethylene glycol chains.

Main Results:

Electron-withdrawing substituents were found to inhibit photoisomerization.
Incorporation of an oligoethylene glycol chain enabled reversible photoisomerization.
The modified switches demonstrated acidochromic switching, accessing six photo- and stereo-isomer combinations.

Conclusions:

Indolinooxazolidines can function as multistate molecular switches.
Precise control over photo- and stereo-isomerism is achievable.
These switches hold promise for developing multi-bit molecular architectures and advanced responsive materials.