Functional Imaging with Chemically Amplified Resists and Organic Molecules

Vekselman, Alexander M.; Zhang, Chunhao; Darling, Graham D.

doi:10.1021/cm960136p

Cited by 26 publications

(22 citation statements)

References 19 publications

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“…These include protonation induced by a photoacid generator, [6,9,12,15,16] as well as chemical amplification catalyzed by a photoacid generator. [3,[17][18][19][20][21][22] Most of these preparation methods are based on photogenerated acids, although other methods precluding the use of photoacid generators have also been reported such as the photobleaching of fluorescent polymers. [7,13,14,23,24] Photobase generators are a group of compounds that produce a base upon irradiation.…”

Section: Introductionmentioning

confidence: 99%

Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Chae

Kim

2007

Adv Funct Materials

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Bicolor fluorescent micro‐patterns in the polymer film are prepared through the use of a new group of photobase generator containing phthalimido carbamate groups. The photobase generation from phthalimide carbamates is studied by examining the changes in pH, fluorescence intensity, and photo‐crosslinking of poly(glycidyl methacrylate). The product analysis of a model compound indicates that amine groups are produced from the photolytic cleavage of the C–N bond of the phthalimide carbamate groups. A copolymer containing phthalimide carbamate groups is applied to a bicolor fluorescent imaging material. Red‐yellow fluorescent micropatterns are obtained by treating the copolymer film, which is irradiated with 254 nm UV light through a photomask, with fluorescamine and rhodamine, consecutively. Various colored fluorescent micropatterns – green, red, or red‐yellow, are obtained on a single polymer film by varying the excitation wavelength.

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Section: Introductionmentioning

confidence: 99%

Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Chae

Kim

2007

Adv Funct Materials

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“…The polymer has an average molecular weight (M w ) of 24 000 compared to a polystyrene standard by gel permeation chromatography (GPC) (polydispersity (PD) = 1.64). Interestingly, the composition of the copolymer obtained, P(tBQMA/MMA) (8), was confirmed to have almost the same molar ratio as the monomer feed ratio by 1 H NMR and thermal analysis. Polymer 8 is soluble in common organic solvents (such as chloroform, THF, and dimethylformamide (DMF)) except for hexane and methanol.…”

mentioning

confidence: 87%

“…[1,2] GaN can be prepared by various routes, for example, salt metathesis reactions. [3,4] Precursors are widely used for the growth of thin GaN films by chemical vapor deposition (CVD) and molecular beam epitaxy (MBE).…”

mentioning

confidence: 99%

Synthesis of and Fluorescent Imaging with a Polymer Having t-BOC-Protected Quinizarin Moieties

Kim¹,

Chang

Kang

et al. 1999

Adv. Mater.

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The generation of patterned images in polymer films has been extensively studied and used in fundamental and applied research areas. The development of patterned color or fluorescent images, especially, is of great technological importance in the electronics industry. Recently, the generation of functional images by selective immobilization of organic dyes in the polymer film has been reported. [1±3] Selective removal of acid-labile protecting groups through photoinduced chemical transformation followed by chemisorption of organic dyes from solution into the patterned polymer film has given micrometer-scale functional images. The two-step procedures described in the literature, however, have potential problems such as difficulty of dye penetration into polymer matrices and concern about longterm stability of the patterned images.To avoid these limitations, we have tried to develop a direct method of generating fluorescence images with a precursor molecule. The strategic basis for designing a precursor is that the precursor molecule is non-fluorescent and/or colorless, but becomes fluorescent and/or reveals color by photoinduced chemical changes. We have previously reported that the UV absorption maximum and fluorescence of quinizarin 1 can be readily altered and manipulated simply by blocking the intramolecular hydrogen bonds.[4] Thus, the UV absorption maximum (479 nm) of quinizarin 1 shifts to a shorter wavelength (335 nm) on blocking the two phenols with two tert-butoxycarbonyl (t-BOC) groups. In addition, the t-BOC-protected quinizarin 2 has virtually no fluorescence, whereas quinizarin 1 is strongly fluorescent due to the quasi-aromatic structure caused by intramolecular hydrogen bonding. As a part of our continuing interest in the generation of relief and functional images with transiently protected precursor molecules in polymer films, we now report the synthesis of a novel polymer having t-BOC-protected quinizarin moieties and the generation of color and fluorescent images by photolithographic methods. To our knowledge, this is the first example of finely resolved fluorescent images with a polymer having transiently protected precursor pendants. The strategies employed for the synthesis of t-BOC-protected quinizarin monomer 7 are shown in Scheme 1. Aldol condensation of leucoquinizarin (3) with 5-(benzyloxy)pentanal (4) [5] in the presence of piperidinium acetate in 2-propanol under Marschalk conditions [6] readily afforded the

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“…[7][8][9][10][11][12][13] Formation of an image can be achieved by irradiating through a mask a thin film of polymer containing a photoinitiator and a dye, the fluorescence properties of which are altered by interaction with the initiator. Typically, the result is a finely resolved fluorescent image in which certain areas of the film are highly fluorescent and others are virtually nonemissive; although bicolor fluorescence imaging is also known.…”

Section: Introductionmentioning

confidence: 99%

Mapping Acid‐Catalyzed Deprotection in Thin Polymer Films: Fluorescence Imaging Using Prefluorescent 7‐Hydroxycoumarin Probes

Frenette¹,

Coenjarts²,

Scaiano³

2004

Macromol. Rapid Commun.

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Summary: Fluorescent images that illustrate acid‐catalyzed tert‐butoxycarbonyl (tBoc) deprotection patterns in polymer films were obtained using fluorescent sensors based on 7‐hydroxycoumarin dyes. Three commercial 7‐hydroxycoumarins, which are highly fluorescent, become practically nonemissive upon protection of the 7‐hydroxyl position with tBoc. In thin polymer films, the protected “prefluorescent” probes can return to their deprotected, fluorescent states by reaction with catalytic amounts of photogenerated acid and mild heating.Protected probes become highly fluorescent after acid‐induced deprotection.magnified imageProtected probes become highly fluorescent after acid‐induced deprotection.

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Functional Imaging with Chemically Amplified Resists and Organic Molecules

Cited by 26 publications

References 19 publications

Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Synthesis of and Fluorescent Imaging with a Polymer Having t-BOC-Protected Quinizarin Moieties

Mapping Acid‐Catalyzed Deprotection in Thin Polymer Films: Fluorescence Imaging Using Prefluorescent 7‐Hydroxycoumarin Probes

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