Design of high efficiency for two-photon polymerization initiator: combination of radical stabilization and large two-photon cross-section achieved by N-benzyl 3,6-bis(phenylethynyl)carbazole derivatives

Xing, Jin Feng; Chen, Weiqiang; Gu, Jie; Dong, Xian Zi; Takeyasu, Nobuyuki; Tanaka, Takuo; Duan, Xuan Ming; Kawata, Satoshi

doi:10.1039/b616792f

Cited by 54 publications

(46 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 3, 5, 6, 8 and 9 have been used previously for their two-photon absorption properties only. 13,14 Compound 3, 4 and 5 have also been used as two-photon fluorescent probes in nonlinear microscopy.…”

Section: Synthesismentioning

confidence: 99%

Molecular engineering of chromophores for combined second-harmonic and two-photon fluorescence in cellular imaging

et al. 2012

Self Cite

View full text Add to dashboard Cite

A series of chromophores with enhanced second-and third-order nonlinear optical properties were engineered for use in combined second-harmonic and two-photon fluorescence microscopy. Electronaccepting moieties imparted nonlinear optical properties to the chromophores. The electron-rich carbazole core served as a template towards one-or two-dimensional chromophores. More efficient acceptor groups (pyridinium, benzazolium, benzothiazolium) on the carbazole donor core resulted in improved second-and third-order nonlinear optical properties. A selection of these chromophores was tested in a cellular environment with a multimodal multiphoton microscope. The structural differences of the chromophores resulted in high selectivity for mitochondria or the nucleus in two-photon fluorescence and ranging from no signal to high selectivity for mitochondria in the SHG channel.

show abstract

Section: Synthesismentioning

confidence: 99%

Molecular engineering of chromophores for combined second-harmonic and two-photon fluorescence in cellular imaging

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…Carbazole with an electron‐rich nitrogen possesses excellent electron donating ability and good optical properties, which make such a chromophore versatile in numerous fields like fluorescent probes . The ease of modification on the aromatic ring enables the construction of conjugated systems with long wavelength absorption and high sensitizing efficiency . Four carbazole‐based oxime esters were designed to investigate the influence of different substitution positions on structure‐reactivity relationships ( 4 a and 4 c ) and to study the impact of different types of radials on the photoinitiating behavior ( 4 a / 4 b and 4 c / 4 d ), respectively.…”

Section: Resultsmentioning

confidence: 99%

Conjugated Bifunctional Carbazole‐Based Oxime Esters: Efficient and Versatile Photoinitiators for 3D Printing under One‐ and Two‐Photon Excitation

Qiu

Naumov

et al. 2020

ChemPhotoChem

View full text Add to dashboard Cite

The rapid development of 3D printing using visible light as an irradiation source requires efficient visible light photoinitiators to realize a fast and reliable 3D printing process. Based on the photocleavage concept, a series of symmetric bifunctional photoinitiators comprising oxime‐ester moieties as latent initiation functionalities and conjugated carbazole as chromophores was synthesized. The impact of substitution position and the types of radicals on photophysical and photochemical behavior was investigated via experimental tests combined with quantum‐chemical calculations. The conjugated carbazole‐based oxime esters exhibit broad absorption bands from 250 to 400 nm and an interesting photobleaching property was observed during photolysis. Under 405 nm LED irradiation, the photoinitiation efficiency of the novel photoinitiators is comparable to that of the commercial visible light photoinitiator TPO. A vertical resolution of 50 μm was obtained when using oxime esters as photoinitiators in DLP 3D printing to fabricate delicate objects. The A‐π‐D‐π‐A core structures impart sufficient two‐photon cross sections (102–136 GM) to the oxime esters, enabling the construction of complex 3D microstructures of nanometer spatial resolution with two‐photon 3D printing technology. Notably, the threshold energy of the formulation containing 4d is lower than that of the commercial two‐photon resists IP−L. Also, the thermal stability of the PIs (>160 °C) is sufficient for daily storage.

show abstract

“…For instance, Hsiue et al investigated a series of carbazole V‐shaped derivatives 28 (Figure ) as two‐dimensional chromophores with large second‐order molecular polarizabilities, which could be translated into macroscopic nonlinearity upon embedding the chromophore into polymeric matrix 53. Derivatives 28 with acetylenic spacers and peripheral formyl and nitro acceptors showed sufficient 2PA activity that allowed their use as two‐photon polymerization initiators 54. Either symmetrically or asymmetrically substituted carbazole D‐(π‐A) 2 molecules 29 and 30 , bearing cyanoacrylic acid or rhodanine‐3‐acetic acid anchoring/acceptor groups (A), also found application as dyes suitable for DSSCs.…”

Section: V‐shaped Moleculesmentioning

confidence: 99%

Alphabet‐Inspired Design of (Hetero)Aromatic Push–Pull Chromophores

Klikar

Solanke

Tydlitát

et al. 2016

The Chemical Record

View full text Add to dashboard Cite

Push-pull molecules represent a unique and fascinating class of organic p-conjugated materials. Herein, we provide a summary of their recent extraordinary design inspired by letters of the alphabet, especially focusing on H-, L-, T-, V-, X-, and Y-shaped molecules. Representative structures from each class were presented and their fundamental properties and prospective applications were discussed. In particular, emphasis is given to molecules recently prepared in our laboratory with T-, X-, and Y-shaped arrangements based on indan-1,3-dione, benzene, pyridine, pyrazine, imidazole, and triphenylamine. These push-pull molecules turned out to be very efficient charge-transfer chromophores with tunable properties suitable for second-order nonlinear optics, two-photon absorption, reversible pH-induced and photochromic switching, photocatalysis, and intercalation.

show abstract

Design of high efficiency for two-photon polymerization initiator: combination of radical stabilization and large two-photon cross-section achieved by N-benzyl 3,6-bis(phenylethynyl)carbazole derivatives

Cited by 54 publications

References 33 publications

Molecular engineering of chromophores for combined second-harmonic and two-photon fluorescence in cellular imaging

Molecular engineering of chromophores for combined second-harmonic and two-photon fluorescence in cellular imaging

Conjugated Bifunctional Carbazole‐Based Oxime Esters: Efficient and Versatile Photoinitiators for 3D Printing under One‐ and Two‐Photon Excitation

Alphabet‐Inspired Design of (Hetero)Aromatic Push–Pull Chromophores

Contact Info

Product

Resources

About