Long alkyl side-chains impede exciton interaction in organic light harvesting crystals

Nagarajan, Kalaivanan; Gopan, Gopika; Cheriya, Rijo T.; Hariharan, Mahesh

doi:10.1039/c7cc02322g

Cited by 21 publications

(10 citation statements)

References 21 publications

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“…Such ultralong phosphorescence shows steady-state optical behavior. [25] To the best of our knowledge,r esearchers have yet to find am olecular system capable of dynamic ultralong phosphorescence.I nspired by the rational manipulation of molecular stacking by alkyl-chain engineering [26] and dynamic motion in crystalline molecule machines, [27] we speculate herein that dynamic organic phosphorescence might be induced by harvesting the synergistic effects of intermolecular interactions and molecular motion within an ew class of molecular rotors resting in the crystalline state.B ymeans of photoirradiation in the crystalline state to manipulate intermolecular interactions,d ynamic optical behavior may be realized to stabilize triplet excitons for ultralong phosphorescence through molecular motion.…”

mentioning

confidence: 99%

Dynamic Ultralong Organic Phosphorescence by Photoactivation

Shi

et al. 2018

Angewandte Chemie

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Smart materials with ultralong phosphorescence are rarely investigated and reported. Herein we report on a series of molecules with unique dynamic ultralong organic phosphorescence (UOP) features, enabled by manipulating intermolecular interactions through UV light irradiation. Our experimental data reveal that prolonged irradiation of single‐component organic phosphors of PCzT, BCzT, and FCzT under ambient conditions can activate UOP with emission lifetimes spanning from 1.8 to 1330 ms. These phosphors can also be deactivated back to their original states with short‐lived phosphorescence by UV irradiation for 3 h at room temperature or through thermal treatment. Additionally, the dynamic UOP was applied successfully for a visual anti‐counterfeiting application. These findings may provide unique insight into dynamic molecular motion for optical processing and expand the scope of smart‐response materials for broader applications.

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confidence: 99%

Dynamic Ultralong Organic Phosphorescence by Photoactivation

Shi

et al. 2018

Angewandte Chemie

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“…The latter approach relies on the fact that changing the alkyl chain length of a molecular system could tune the crystal packing mode and thus the electronic properties in the solid-state. [19][20][21][22] The results reported herein show that the combined treatments of mechanical grinding and aniline vapor fuming on PAP-Cn (n = 4, 8, 12, or 16) result in the formation of a three-component PAP-Cn/PAP-Cn/ aniline complex (triplex). In addition, mechanical grinding increases the retention time for the aniline guest in the films.…”

Section: Introductionmentioning

confidence: 73%

Mechanochromic and vapochromic fluorescence of a bulky π‐system: Alkyl chain‐length effects, triplex emission, and differential sensing of aniline vapors

Lee

Hsu

Lien

et al. 2020

J Chinese Chemical Soc

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The interplay of mechanical grinding and aniline vapor fuming on the fluorescence of the pentiptycene-anthracene-pentiptycene π-conjugated molecules PAP-Cn, where n is 4, 8, 12, or 16 and refers to the number of carbon atom in the terminal alkyl chains, in solid films are reported. The differences and similarities among the four homologs have led to a conclusion of the formation of an emissive triplex state for the ground and fumed films. Thermogravimetric analysis reveals the guest-host molar ratio and the retention ability of the aniline on the various types of films. A stepwise protocol of fuming-grindingannealing is developed for fluorimetric differential sensing of eight substituted aniline vapors with a single probe of PAP-C8. The role of the bulky pentiptycene groups in the observed fluorescence properties is also discussed.

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“…In this context, the intriguing polymorph-dependentP MFC properties of 1-C8 prompted us to furtheri nvestigate the crystal polymorphisma nd both the local and bulk photomechanical effects of this p system.O ne of our approaches is to vary the alkyl chain length,a st his has been au seful strategy for structurala nd property engineering of solid-state materials. [36][37][38] Accordingly,c ompounds 1-Cn (n = 4, 7-13, 16), where n refers to the number of carbon atoms in the linear alkyl chain, were studied. The results reported herein show that the alkyl chain length affects not only the crystal packing mode but also the lattice stiffness.…”

Section: Introductionmentioning

confidence: 99%

Alkyl Chain Length‐ and Polymorph‐Dependent Photomechanochromic Fluorescence of Anthracene Photodimerization in Molecular Crystals: Role of the Lattice Stiffness

Kuo

Hsu

Chen

et al. 2020

Chemistry A European J

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Anthracene–pentiptycene hybrid systems 1‐Cn, where n refers to the number of carbon atoms in the linear alkyl chain, crystallize in three different polymorphs, denoted Y (yellow), G (green), and B (blue) forms in terms of the fluorescence color. While all Y‐form crystals show the same yellow‐to‐blue fluorescence color response to the photomechanical stress generated by the anthracene [4+4] photodimerization reaction, the four G forms exhibit distinct photomechanofluorochromism (PMFC): from green to blue for G‐1‐C4, to orange for G‐1‐C7, to red for G‐1‐C8, and to red then blue for G‐1‐C9, and the B forms show no photochromic activity. The intriguing RGB three‐color PMFC and abnormal topochemical reactivity of G‐1‐C9 are attributed to inherent softness of the crystal lattice.

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Long alkyl side-chains impede exciton interaction in organic light harvesting crystals

Cited by 21 publications

References 21 publications

Dynamic Ultralong Organic Phosphorescence by Photoactivation

Dynamic Ultralong Organic Phosphorescence by Photoactivation

Mechanochromic and vapochromic fluorescence of a bulky π‐system: Alkyl chain‐length effects, triplex emission, and differential sensing of aniline vapors

Alkyl Chain Length‐ and Polymorph‐Dependent Photomechanochromic Fluorescence of Anthracene Photodimerization in Molecular Crystals: Role of the Lattice Stiffness

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