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Title: Red phosphorescence from benzo[2,1,3]thiadiazoles at room temperature

Abstract

In this paper, we describe the red phosphorescence exhibited by a class of structurally simple benzo[2,1,3]thiadiazoles at room temperature. The photophysical properties of these molecules in deoxygenated cyclohexane, including their absorption spectra, steady-state photoluminescence and excitation spectra, and phosphorescence lifetimes, are presented. Finally, time-dependent density functional theory calculations were carried out to better understand the electronic excited states of these benzo[2,1,3]thiadiazoles and why they are capable of phosphorescence.

Authors:
 [1];  [1];  [1];  [1];  [1]
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  1. Massachusetts Inst. of Technology, Cambridge, MA (United States)
Publication Date:
Research Org.:
Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1344917
Grant/Contract Number:  
FG02-07ER46474
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Organic Chemistry
Additional Journal Information:
Journal Volume: 81; Journal Issue: 11; Journal ID: ISSN 0022-3263
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Gutierrez, Gregory D., Sazama, Graham T., Wu, Tony, Baldo, Marc A., and Swager, Timothy M. Red phosphorescence from benzo[2,1,3]thiadiazoles at room temperature. United States: N. p., 2016. Web. doi:10.1021/acs.joc.6b00789.
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Gutierrez, Gregory D., Sazama, Graham T., Wu, Tony, Baldo, Marc A., & Swager, Timothy M. Red phosphorescence from benzo[2,1,3]thiadiazoles at room temperature. United States. https://doi.org/10.1021/acs.joc.6b00789
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Gutierrez, Gregory D., Sazama, Graham T., Wu, Tony, Baldo, Marc A., and Swager, Timothy M. Mon . "Red phosphorescence from benzo[2,1,3]thiadiazoles at room temperature". United States. https://doi.org/10.1021/acs.joc.6b00789. https://www.osti.gov/servlets/purl/1344917.
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@article{osti_1344917,
title = {Red phosphorescence from benzo[2,1,3]thiadiazoles at room temperature},
author = {Gutierrez, Gregory D. and Sazama, Graham T. and Wu, Tony and Baldo, Marc A. and Swager, Timothy M.},
abstractNote = {In this paper, we describe the red phosphorescence exhibited by a class of structurally simple benzo[2,1,3]thiadiazoles at room temperature. The photophysical properties of these molecules in deoxygenated cyclohexane, including their absorption spectra, steady-state photoluminescence and excitation spectra, and phosphorescence lifetimes, are presented. Finally, time-dependent density functional theory calculations were carried out to better understand the electronic excited states of these benzo[2,1,3]thiadiazoles and why they are capable of phosphorescence.},
doi = {10.1021/acs.joc.6b00789},
journal = {Journal of Organic Chemistry},
number = 11,
volume = 81,
place = {United States},
year = {Mon May 23 00:00:00 EDT 2016},
month = {Mon May 23 00:00:00 EDT 2016}
}
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https://doi.org/10.1021/acs.joc.6b00789
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Figures / Tables:

Figure 1 Figure 1: Photophysical properties of phosphorescent compounds 1-Br and 1-I in cyclohexane. (a) 1-Br and (d) 1-I and their appearance in degassed cyclohexane under normal and UV (λ = 365 nm) lighting. (b) Absorption spectrum and photoluminescence spectra under air and N2 gas for 1-Br and (e) 1-I (λex =more » 370 nm). (c) Phosphorescence excitation spectrum of 1-Br and (f) 1-I (λem = 575 nm). Photoluminescence and excitation spectra were measured for 50 μM solutions. A small peak attributed to Raman scattering (λmax = 414 nm) of the excitation beam by the solvent overlaps with the fluorescence of all phosphorescent samples presented in this study and is not considered in our analysis.« less
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      Table 1 (p. 18)table
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