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Aggregation-induced emission and aggregation-promoted photochromism of bis(diphenylmethylene)dihydroacenes.

ABSTRACT: Reported herein is a new class of pure polycyclic hydrocarbon molecules, designed through a novel aggregation-induced emission (AIE) strategy, with unexpected photochromic properties. The restriction of intramolecular motion was found as a comprehensive mechanism for the AIE effect. The photochromism mechanism study revealed that the photocyclization reaction of cis-stilbene, the molecular conformation in the single crystal and the tetracene backbone should contribute to the unique photo behavior. In particular, the fast responsive, photo-reversible and thermo-irreversible photochromic effect facilitated in the solid state opens a new field of aggregation-promoted photochromism.

SUBMITTER: He Z

PROVIDER: S-EPMC5500900 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Aggregation-induced emission and aggregation-promoted photochromism of bis(diphenylmethylene)dihydroacenes.

He Zikai Z Shan Liang L Mei Ju J Wang Hong H Lam Jacky W Y JWY Sung Herman H Y HHY Williams Ian D ID Gu Xiao X Miao Qian Q Tang Ben Zhong BZ

Chemical science 20150403 6

Reported herein is a new class of pure polycyclic hydrocarbon molecules, designed through a novel aggregation-induced emission (AIE) strategy, with unexpected photochromic properties. The restriction of intramolecular motion was found as a comprehensive mechanism for the AIE effect. The photochromism mechanism study revealed that the photocyclization reaction of <i>cis</i>-stilbene, the molecular conformation in the single crystal and the tetracene backbone should contribute to the unique photo ...[more]

PMID: 28717460

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Project description:It is extremely challenging but desirable to regulate the photophysical and photochemical processes of aggregation-induced emission luminogens (AIEgens) in distinct states in a controllable manner. Herein, we design two groups of AIEgens based on a triphenylacrylonitrile (TPAN) skeleton with through-space conjugation (TSC) property, demonstrate controlled regulation of photophysical emission efficiency/color and photochemical photochromic and photoactivatable fluorescence behaviours of these compounds, and further validate design principles to achieve highly efficient and emission-tuning AIEgens and to accomplish photo-dependent color switches and fluorescence changes. It is surprisingly found that the introduction of heavy halogens like bromine into a TPAN skeleton dramatically enhances the emission efficiency, and such an abnormal phenomenon against the heavy-atom effect is attributed to the specific through-space conjugation nature of the AIE-active skeleton, effective intermolecular halogen-bond-induced restriction of intramolecular motions, and heavy atom-induced vibration reduction. The incorporation of two electron-donating amino groups into the TPAN skeleton cause the luminogens to undergo a bathochromic shifted emission due to the formation of a D-A pattern. Apart from the regulation of photophysical processes in the solid state, the construction of the D-A pattern in luminogens also results in extremely different photochemical reactions accompanying reversible/irreversible photochromism and photoactivatable fluorescence phenomena in a dispersed state. It is revealed that photo-triggered cyclization and decyclization reactions dominantly contribute to reversible photochromism of the TPAN family, and the photo-induced cyclization-dehydrogenation reaction is responsible for the irreversible color changes and photoactivatable fluorescence behaviours of the NTPAN family. The demonstrations of multiple-mode signaling in photoswitchable patterning and information encryption highlight the importance of controlled regulation of photophysics and photochemistry of fused chromic and AIE-active luminogens in distinct states.

Dataset Information

Aggregation-induced emission and aggregation-promoted photochromism of bis(diphenylmethylene)dihydroacenes.

Publications

Aggregation-induced emission and aggregation-promoted photochromism of bis(diphenylmethylene)dihydroacenes.

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