Negatively Photochromic Organic Compounds: Exploring the Dark Side

Stuart Aiken, Ross Edgar, Christopher Gabbutt, B. Mark Heron, Peter A. Hobson

Research output: Contribution to journalReview article

15 Citations (Scopus)

Abstract

The last few years have seen an explosion of interest in traditional photochromic systems not only for their applications in variable transmission devices, which continues to attract commercial interest, but also for the ability of these molecules to undergo structural and electronic reorganisation which has been seized upon by materials scientists for the development of switches, logic gates, photoinduced molecular motions such as rotors and fibrils, and photoregulation of drug availability. This comprehensive review examines, for the first time, the ‘dark side of photochromism’; negatively photochromic systems which are coloured in their ground state and reversibly photobleach upon exposure to electromagnetic radiation with a wavelength over ca. 400 nm i.e. visible light responsive systems. This review is organised by structural class and examines their synthesis, structure, key spectroscopic data for coloured and bleached species, structure – switching relationships and applications. The usefulness of these negatively photochromic systems is only gradually coming to the fore with the advantages of low energy activation c.f. conventional Uv-activated switches, enabling the modulation of a plethora of useful optical and physical properties and the design of new materials with broad ranging applications.
LanguageEnglish
Pages92-121
Number of pages30
JournalDyes and Pigments
Volume149
Early online date27 Sep 2017
DOIs
Publication statusPublished - Feb 2018

Fingerprint

Organic compounds
Switches
Photochromism
Logic gates
Electromagnetic waves
Ground state
Explosions
Optical properties
Activation energy
Physical properties
Rotors
Modulation
Availability
Wavelength
Molecules
Pharmaceutical Preparations

Cite this

@article{816b2bd9e3104b909a1446acb9c36d33,
title = "Negatively Photochromic Organic Compounds: Exploring the Dark Side",
abstract = "The last few years have seen an explosion of interest in traditional photochromic systems not only for their applications in variable transmission devices, which continues to attract commercial interest, but also for the ability of these molecules to undergo structural and electronic reorganisation which has been seized upon by materials scientists for the development of switches, logic gates, photoinduced molecular motions such as rotors and fibrils, and photoregulation of drug availability. This comprehensive review examines, for the first time, the ‘dark side of photochromism’; negatively photochromic systems which are coloured in their ground state and reversibly photobleach upon exposure to electromagnetic radiation with a wavelength over ca. 400 nm i.e. visible light responsive systems. This review is organised by structural class and examines their synthesis, structure, key spectroscopic data for coloured and bleached species, structure – switching relationships and applications. The usefulness of these negatively photochromic systems is only gradually coming to the fore with the advantages of low energy activation c.f. conventional Uv-activated switches, enabling the modulation of a plethora of useful optical and physical properties and the design of new materials with broad ranging applications.",
keywords = "Photochromism, Negative photochromism, Spirobenzopyran, Napthoxazine, Thioindigoid, Dithienylethene, Dihydropyrene, Switches, Logic gates, Naphthoxazine",
author = "Stuart Aiken and Ross Edgar and Christopher Gabbutt and Heron, {B. Mark} and Hobson, {Peter A.}",
year = "2018",
month = "2",
doi = "10.1016/j.dyepig.2017.09.057",
language = "English",
volume = "149",
pages = "92--121",
journal = "Dyes and Pigments",
issn = "0143-7208",
publisher = "Elsevier BV",

}

Negatively Photochromic Organic Compounds : Exploring the Dark Side. / Aiken, Stuart; Edgar, Ross; Gabbutt, Christopher; Heron, B. Mark; Hobson, Peter A.

In: Dyes and Pigments, Vol. 149, 02.2018, p. 92-121.

Research output: Contribution to journalReview article

TY - JOUR

T1 - Negatively Photochromic Organic Compounds

T2 - Dyes and Pigments

AU - Aiken, Stuart

AU - Edgar, Ross

AU - Gabbutt, Christopher

AU - Heron, B. Mark

AU - Hobson, Peter A.

PY - 2018/2

Y1 - 2018/2

N2 - The last few years have seen an explosion of interest in traditional photochromic systems not only for their applications in variable transmission devices, which continues to attract commercial interest, but also for the ability of these molecules to undergo structural and electronic reorganisation which has been seized upon by materials scientists for the development of switches, logic gates, photoinduced molecular motions such as rotors and fibrils, and photoregulation of drug availability. This comprehensive review examines, for the first time, the ‘dark side of photochromism’; negatively photochromic systems which are coloured in their ground state and reversibly photobleach upon exposure to electromagnetic radiation with a wavelength over ca. 400 nm i.e. visible light responsive systems. This review is organised by structural class and examines their synthesis, structure, key spectroscopic data for coloured and bleached species, structure – switching relationships and applications. The usefulness of these negatively photochromic systems is only gradually coming to the fore with the advantages of low energy activation c.f. conventional Uv-activated switches, enabling the modulation of a plethora of useful optical and physical properties and the design of new materials with broad ranging applications.

AB - The last few years have seen an explosion of interest in traditional photochromic systems not only for their applications in variable transmission devices, which continues to attract commercial interest, but also for the ability of these molecules to undergo structural and electronic reorganisation which has been seized upon by materials scientists for the development of switches, logic gates, photoinduced molecular motions such as rotors and fibrils, and photoregulation of drug availability. This comprehensive review examines, for the first time, the ‘dark side of photochromism’; negatively photochromic systems which are coloured in their ground state and reversibly photobleach upon exposure to electromagnetic radiation with a wavelength over ca. 400 nm i.e. visible light responsive systems. This review is organised by structural class and examines their synthesis, structure, key spectroscopic data for coloured and bleached species, structure – switching relationships and applications. The usefulness of these negatively photochromic systems is only gradually coming to the fore with the advantages of low energy activation c.f. conventional Uv-activated switches, enabling the modulation of a plethora of useful optical and physical properties and the design of new materials with broad ranging applications.

KW - Photochromism

KW - Negative photochromism

KW - Spirobenzopyran

KW - Napthoxazine

KW - Thioindigoid

KW - Dithienylethene

KW - Dihydropyrene

KW - Switches

KW - Logic gates

KW - Naphthoxazine

UR - http://www.sciencedirect.com/science/journal/01437208?sdc=1

UR - http://www.scopus.com/inward/record.url?scp=85030483908&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2017.09.057

DO - 10.1016/j.dyepig.2017.09.057

M3 - Review article

VL - 149

SP - 92

EP - 121

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

ER -