Synthesis and Characterization of New Truxenones for Nonlinear Optical Applications

Sanguinet, Lionel; Williams, Jarrod; Yang, Zhiyong; Twieg, Robert J.; Mao, Guilin; Singer, Kenneth D.; Wiggers, Greg; Petschek, Rolfe G.

doi:10.1021/cm0601887

Cited by 60 publications

(27 citation statements)

References 35 publications

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“…These compounds have been extensively studied in the literature, especially for the design of highly soluble planar heptacyclic polyarene structures (10,15-dihydro-5 H -diindeno[1,2- a ;1′,2′- c ]fluorene), more commonly known as truxenes, that result from the trimerization of three indan-1-one units47. By increasing the content of ketone units per trimerizable units, similarly trimerization of indanedione derivatives can furnish truxenone analogues with three keto groups at the inner positions48. While generating symmetrical units such as in the case of INDO 4 , bifunctional tetraketoindacenes open the way towards carbonyl-functionalized microporous ladder polymers49.…”

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confidence: 99%

On-surface synthesis of aligned functional nanoribbons monitored by scanning tunnelling microscopy and vibrational spectroscopy

Kalashnyk

Mouhat

et al. 2017

Nat Commun

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In the blooming field of on-surface synthesis, molecular building blocks are designed to self-assemble and covalently couple directly on a well-defined surface, thus allowing the exploration of unusual reaction pathways and the production of specific compounds in mild conditions. Here we report on the creation of functionalized organic nanoribbons on the Ag(110) surface. C–H bond activation and homo-coupling of the precursors is achieved upon thermal activation. The anisotropic substrate acts as an efficient template fostering the alignment of the nanoribbons, up to the full monolayer regime. The length of the nanoribbons can be sequentially increased by controlling the annealing temperature, from dimers to a maximum length of about 10 nm, limited by epitaxial stress. The different structures are characterized by room-temperature scanning tunnelling microscopy. Distinct signatures of the covalent coupling are measured with high-resolution electron energy loss spectroscopy, as supported by density functional theory calculations.

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confidence: 99%

On-surface synthesis of aligned functional nanoribbons monitored by scanning tunnelling microscopy and vibrational spectroscopy

Kalashnyk

Mouhat

et al. 2017

Nat Commun

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“…Truxenone and F 3 -truxenone were synthesised following literature procedures 19,20 and triply puried by thermal gradient sublimation before degassing 20 C below the evaporation temperature for several days. 21 NMR data and full synthesis details are presented in the ESI (S1 and S2).…”

Section: Methodsmentioning

confidence: 99%

The effect of fluorination on the surface structure of truxenones

et al. 2016

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“…Noticeably, examples of dyes based on 1H-cyclopentanaphthalene-1,3-dione are extremely scarce in literature [42,[54][55][56][57], evidencing the interest and the novelty of the structures proposed in this work. Interestingly, their good light absorption properties @405 nm were anticipated by theoretical calculations and molecular design.…”

Section: Introductionmentioning

confidence: 95%

Free Radical Photopolymerization and 3D Printing Using Newly Developed Dyes: Indane-1,3-Dione and 1H-Cyclopentanaphthalene-1,3-Dione Derivatives as Photoinitiators in Three-Component Systems

et al. 2020

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The design of photoinitiating systems with excellent photochemical reactivities at 405nm LED is one of the obstacles to efficiently promote free radical polymerization in mild conditions (e.g., low light intensity, under air). Here, our actual search for new multicomponent photoinitiating systems at 405nm LED prompts us to develop new dyes based on push–pull structures. In the present paper, we chose two series of new dyes which possess indane-1,3-dione and 1H-cyclopenta naphthalene-1,3-dione groups as the electron-withdrawing groups, since they have the great potential to behave as sensitive and remarkable photoinitiators in vat photopolymerization/3D printing. When incorporated with a tertiary amine (ethyl dimethylaminobenzoate EDB, used as electron/hydrogen donor) and an iodonium salt (used as electron acceptor) as the three-component photoinitiating systems (PISs), and among a series of 21 dyes, 10 of them could efficiently promote the free radical photopolymerization of acrylates. Interestingly, steady state photolysis experiments revealed different behaviors of the dyes. Fluorescence experiments and free energy change calculations for redox processes were also carried out to investigate the relevant chemical mechanisms. Additionally, the formation of radicals from the investigated PISs was clearly observed by electron spin resonance (ESR) spin-trapping experiments. Finally, stereoscopic 3D patterns were successfully fabricated by the laser writing technique. In this work, the use of push–pull dyes based on the naphthalene scaffold as photoinitiators of polymerization is reported for the first time in a systematic study aiming at investigating the structure–performance relationship for irradiation carried out at 405 nm. By carefully selecting the electron donors used in the two series of push–pull dyes, novel and high-performance photoinitiating systems operating at 405 nm are thus proposed.

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Synthesis and Characterization of New Truxenones for Nonlinear Optical Applications

Cited by 60 publications

References 35 publications

On-surface synthesis of aligned functional nanoribbons monitored by scanning tunnelling microscopy and vibrational spectroscopy

On-surface synthesis of aligned functional nanoribbons monitored by scanning tunnelling microscopy and vibrational spectroscopy

The effect of fluorination on the surface structure of truxenones

Free Radical Photopolymerization and 3D Printing Using Newly Developed Dyes: Indane-1,3-Dione and 1H-Cyclopentanaphthalene-1,3-Dione Derivatives as Photoinitiators in Three-Component Systems

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