Synthesis and Optical Properties of Photochromic Perinaphthothioindigo

PDF Version Also Available for Download.

Description

(1,2-naphtho)(1,8-naphtho)thioindigo (PNT) has been synthesized following a simple Friedel-Crafts route and its photochemical properties in toluene and PMMA characterized. PNT is a photochromic molecule capable of reversible photoisomerization between a yellow form (cis-PNT, {lambda}{sub max} = 484 nm) and a purple form (trans-PNT, {lambda}{sub max} = 595 nm). The stable purple form converts to the yellow form with a trans-PNT to cis-PNT conversion quantum yield of 0.027 in toluene and 0.062 in PMMA. The unstable yellow form exhibits a cis-PNT to trans-PNT quantum efficiency of conversion of 0.27-0.85 in toluene and 0.17-0.68 PMMA, with highest conversion efficiency occurring in the ... continued below

Physical Description

PDF-FILE: 25 ; SIZE: 1.4 MBYTES pages

Creation Information

Cherepy, N J & Sanner, R D February 10, 2005.

Context

This report is part of the collection entitled: Office of Scientific & Technical Information Technical Reports and was provided by UNT Libraries Government Documents Department to Digital Library, a digital repository hosted by the UNT Libraries. More information about this report can be viewed below.

Who

People and organizations associated with either the creation of this report or its content.

Sponsor

Publisher

Provided By

UNT Libraries Government Documents Department

Serving as both a federal and a state depository library, the UNT Libraries Government Documents Department maintains millions of items in a variety of formats. The department is a member of the FDLP Content Partnerships Program and an Affiliated Archive of the National Archives.

Contact Us

What

Descriptive information to help identify this report. Follow the links below to find similar items on the Digital Library.

Description

(1,2-naphtho)(1,8-naphtho)thioindigo (PNT) has been synthesized following a simple Friedel-Crafts route and its photochemical properties in toluene and PMMA characterized. PNT is a photochromic molecule capable of reversible photoisomerization between a yellow form (cis-PNT, {lambda}{sub max} = 484 nm) and a purple form (trans-PNT, {lambda}{sub max} = 595 nm). The stable purple form converts to the yellow form with a trans-PNT to cis-PNT conversion quantum yield of 0.027 in toluene and 0.062 in PMMA. The unstable yellow form exhibits a cis-PNT to trans-PNT quantum efficiency of conversion of 0.27-0.85 in toluene and 0.17-0.68 PMMA, with highest conversion efficiency occurring in the vicinity of its {lambda}{sub max} of 484 nm. Trans-PNT has a strong fluorescence quantum yield, 0.14 (toluene) and 0.16 (PMMA). For samples prepared photochemically in the cis-PNT form, slow thermal relaxation to the trans form occurs in the dark, with a half life of about 17 hours in toluene (25 C) and even slower, 168 hours, in PMMA. The property of photoswitching between fluorescent and non-fluorescent forms makes this material a candidate for many applications in imaging and data storage. An anomalous excitation profile for the fluorescence from trans-PNT, showing a dip at {approx}600 nm, is an agreement with the wavelength-dependent quantum yield of conversion from trans-PNT to cis-PNT, which is highest at the absorbance peak.

Physical Description

PDF-FILE: 25 ; SIZE: 1.4 MBYTES pages

Source

  • Other Information: PBD: 10 Feb 2005

Language

Item Type

Identifier

Unique identifying numbers for this report in the Digital Library or other systems.

  • Report No.: UCRL-TR-209725
  • Grant Number: W-7405-ENG-48
  • DOI: 10.2172/15016022 | External Link
  • Office of Scientific & Technical Information Report Number: 15016022
  • Archival Resource Key: ark:/67531/metadc1411127

Collections

This report is part of the following collection of related materials.

Office of Scientific & Technical Information Technical Reports

Reports, articles and other documents harvested from the Office of Scientific and Technical Information.

Office of Scientific and Technical Information (OSTI) is the Department of Energy (DOE) office that collects, preserves, and disseminates DOE-sponsored research and development (R&D) results that are the outcomes of R&D projects or other funded activities at DOE labs and facilities nationwide and grantees at universities and other institutions.

What responsibilities do I have when using this report?

When

Dates and time periods associated with this report.

Creation Date

  • February 10, 2005

Added to The UNT Digital Library

  • Jan. 23, 2019, 12:54 p.m.

Description Last Updated

  • Feb. 8, 2019, 3:54 p.m.

Usage Statistics

When was this report last used?

Yesterday: 0
Past 30 days: 1
Total Uses: 1

Interact With This Report

Here are some suggestions for what to do next.

Start Reading

PDF Version Also Available for Download.

International Image Interoperability Framework

IIF Logo

We support the IIIF Presentation API

Cherepy, N J & Sanner, R D. Synthesis and Optical Properties of Photochromic Perinaphthothioindigo, report, February 10, 2005; Livermore, California. (https://digital.library.unt.edu/ark:/67531/metadc1411127/: accessed March 18, 2019), University of North Texas Libraries, Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.