Transitions Optical, Inc.

University of Miami

Beckman Coulter, Inc.

Massimiliano Tomasulo

Anil Kumar

Meng He

Francisco M Raymo

Wenjing Xiao

Robert W Walters

Anu Chopra

Darrin R Dabideen

Huayun Yu

Elizabeth Ann Zezinka

Xiao-Man Dai

Sergei Gulnik

Arunkumar Easwaran

Allison Greene

David B Knowles

Barry Van Gemert

Jun Deng

Cory S Brown

Ruisong Xu

Beon-Kyu Kim

Stephen D Straight

Sujit Mondal

Victor A Montes

Jason Ryan Lewis

Shengwen Yuan

Brian R Stepp

Kevin E Bancroft

Eric Spitler

Water-soluble photoactive polymers, included polymer tandem dyes, as described as well as methods for their preparation and use. The photoactive polymers can be prepared by direct modification of core polymers (e.g., violet excitable polymers) with dyes or other functional groups. Methods of detecting analytes using the polymers are also described.

Polymer dye modification and applications

The present invention relates to photochromic indeno fused phenanthrenopyran compounds represented by the following Formula (I). With some embodiments, the photochromic compounds represented by Formula (I) include at least one lengthening group (e.g., Rand/or Reach independently being a lengthening group) and the compounds of the present invention are photochromicdichroic compounds. The present invention also relates to photochromic compositions and photochromic articles, such as photochromic ophthalmic articles that include one or more photochromic compounds represented by Formula (I). 

Photochromic indeno fused phenanthrenopyran compounds

The present invention relates to photochromic compounds, such as thienochromene compounds represented by the following Formulas (1a) and/or (1b). The present invention also relates to photochromic compositions and articles containing one or more such photochromic thienochromene compounds. 

Photochromic thienochromene compounds

A multilayer photochromic article can include a photochromic substrate, which may include a first photochromic layer defining a surface of the substrate, and a second photochromic layer positioned between the surface of the photochromic substrate and a source of actinic radiation, and in which the photochromic substrate and the second photochromic layer are selected such that the fade half-life of the photochromic substrate or the half-life of the first photochromic layer defining the surface of the substrate are greater than the fade half-life of the second photochromic layer.

Multilayer photochromic articles

The present invention relates to methods of preparing fused ring indeno compounds that involves reacting together a dienophile and a lactone compound, in the presence of a catalyst, and a carboxylic acid anhydride. With some embodiments, the fused ring indeno compound is represented by the following Formula (I-A), the dienophile is represented by the following Formula (II-A), and the lactone compound is represented by the following Formula (III-A): 

Method of preparing fused ring indeno compounds

The present invention relates to photochromic indeno-fused ring pyran compounds represented by the following Formula (I-A): The present invention also relates to photochromic dichroic compounds, such as represented by Formula (I-A), in which (i) Zis a group N&#x2014;Rin which Ris a group L, and (ii) optionally at least one Rindependently for each n is selected from a group L, in which the group L independently in each case is a lengthening group that provides the photochromic compound with dichroic properties, in accordance with some embodiments. The present invention also relates to photochromic articles, such as photochromic ophthalmic articles, that include one or more photochromic compounds according to the present invention, such as represented by Formula (I-A).

Photochromic indeno-fused ring pyran compounds

The present invention relates to intermediate compounds represented by the following Formula (I-A), The intermediate compounds of the present invention, such as represented by Formula (I-A), can be used to prepare photochromic compounds, such as photochromic fused ring indenopyran compounds, including but not limited to photochromic fused ring indeno-naphtho-pyran compounds.

Fused ring indeno compounds for preparation of photochromic compounds

The present invention relates to photochromic materials that include one or more indeno-fused naphthopyrans that have particular groups at the 7, 11, and 13 positions thereof, and at the position alpha to the oxygen of the pyran ring thereof. With some embodiments, hydrogen or an alkoxy group is bonded to the 7 position, an optionally substituted phenyl is bonded to the 11 position, two alkyl groups are bonded to the 13 position, and two optionally substituted phenyl groups are bonded to the position alpha to the oxygen of the pyran ring of the indeno-fused naphthopyran compound. The 13 position of the indeno-fused naphthopyrans is free of ether groups in which an ether oxygen is bonded to the 13 position, and hydroxyl. The present invention also relates to photochromic articles and compositions that include such indeno-fused naphthopyrans.

Photochromic materials that include indeno-fused naphthopyrans

Described herein are compounds generally comprising an indeno[2',3&#x2032;:3,4]naptho[1,2-b]pyran structure. Such compounds may be useful for their photochromic properties, and be used in certain photochromic compositions. Such compositions may further comprise other photochromic compositions and/or materials. Additionally, such compounds and/or compositions may be suitable for preparing certain photochromic articles.

Photochromic compounds and compositions

The present invention relates to photochromic materials that include a photochromic compound that includes a photochromic substituent (e.g., an indeno-fused naphthopyran) and at least one pendent silane group, which is bonded to the photochromic substituent. The pendent silane groups are selected from certain pendent siloxy-silane groups and/or pendent alkoxy-silane groups represented by general formulas (I) and/or (II) as described in further detail herein. The present invention also relates to photochromic articles, such as photochromic optical elements (e.g., photochromic lenses), and photochromic coating compositions (e.g., curable photochromic coating compositions), that include the photochromic materials of the present invention. The photochromic materials of the present invention have improved compatibility with compositions into which they may be incorporated, for example, coating compositions, such as urethane coating compositions.

Photochromic materials

Heterocyclic compounds incorporating a [1,3]oxazine ring may be used to make chromogenic materials. These molecules switch from a colorless state to a colored form upon addition of either acid or base. In both instances, the [1,3]oxazine ring opens in response to the pH change forming an indolium cation, after the addition of acid, or a phenolate anion, after the addition of base. Alternatively, the switch may occur in response to a change in electrical current or potential or a change in temperature. Chromophores absorb in the visible region of the electromagnetic spectrum. Hence, their formation translates into the appearance of color. These processes are fully reversible and the original colorless state can be regenerated by switching the pH back to neutral. Thus, these halochromic compounds can be used to develop displays, filters, indicators, lenses, sensors, switches, or windows able to switch their color in response to pH changes.

Use of oxazine compounds for making chromogenic materials

We have designed a molecular switch based on the photoinduced opening and thermal closing of a [1,3]oxazine ring. A substituted [1,3]oxazine compound described as having a general (i.e., unsubstituted) structure with fused indoline and benzooxazine fragments such that they share a common bond in the [1,3]oxazine compound: (i) the bond connecting positions 1 and 2 of the indoline fragment and (ii) the bond connecting positions 2 and 3 of the benzooxazine fragment. Irradiation by light of suitable wavelength and intensity of this photochromic compound induces cleavage of a [C&#x2014;O] bond of the [1,3]oxazine ring to form a phenolate chromophore. The photogenerated (e.g., colored) isomer may revert thermally to the starting (e.g., colorless) oxazine. Alternatively, the switch may be between isomers of the compound that absorb at different wavelengths. Reversible coloration of silica or polymeric materials and switching optical signals may involve many cycles of interconversion between different colored states. A colorless/colored state may be maintained by constant irradiation or chemical trapping.

Photochromic compounds based on ring opening and closing of an [1,3]oxazine compound

A chromogenic oxazine compound for the colorimetric detection of cyanide was designed. Indeed, the [1,3]oxazine ring of our compound opens to form a phenolate chromophore in response to cyanide. The heterocyclic com-pound may be comprised of fused benzooxazine and indoline rings: wherein Ris an alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl), a substituted alkyl, a cycloalkyl (e.g., cyclopentyl, cyclohexyl), a substituted cycloalkyl, an aryl (e.g., phenyl), or a substituted aryl and Ris a chromophore (e.g., nitroso, nitro, azo dyes). This quantitative chromogenic transformation permits the detection of micromolar concentrations of cyanide in water. Furthermore, our chromogenic oxazine is insensitive to the presence of large concentrations of fluoride, chloride, bromide or iodide anions, which are generally the principal interferents in the colorimetric detection of cyanide.

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Monroeville, PA, United States of America

Massimiliano Tomasulo