skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Photophysical characterization and time-resolved spectroscopy of a anthradithiophene dimer: exploring the role of conformation in singlet fission

Abstract

We investigate the singlet fission capability of an anthradithiophene dimer.

Authors:
ORCiD logo [1];  [1];  [2];  [1];  [3];  [1];  [2];  [3];  [2]; ORCiD logo [1]
  1. Department of Chemistry; Princeton University; Princeton; USA
  2. Department of Chemistry; University of Kentucky; Lexington; USA
  3. Department of Chemistry; Columbia University; New York; USA
Publication Date:
Research Org.:
Princeton Univ., NJ (United States); Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1535211
DOE Contract Number:  
SC0015429; SC0012704
Resource Type:
Journal Article
Journal Name:
Physical Chemistry Chemical Physics. PCCP (Print)
Additional Journal Information:
Journal Volume: 19; Journal Issue: 34; Journal ID: ISSN 1463-9076
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
Chemistry; Physics

Citation Formats

Dean, Jacob C., Zhang, Ruomeng, Hallani, Rawad K., Pensack, Ryan D., Sanders, Samuel N., Oblinsky, Daniel G., Parkin, Sean R., Campos, Luis M., Anthony, John E., and Scholes, Gregory D. Photophysical characterization and time-resolved spectroscopy of a anthradithiophene dimer: exploring the role of conformation in singlet fission. United States: N. p., 2017. Web. doi:10.1039/c7cp03774k.
Dean, Jacob C., Zhang, Ruomeng, Hallani, Rawad K., Pensack, Ryan D., Sanders, Samuel N., Oblinsky, Daniel G., Parkin, Sean R., Campos, Luis M., Anthony, John E., & Scholes, Gregory D. Photophysical characterization and time-resolved spectroscopy of a anthradithiophene dimer: exploring the role of conformation in singlet fission. United States. doi:10.1039/c7cp03774k.
Dean, Jacob C., Zhang, Ruomeng, Hallani, Rawad K., Pensack, Ryan D., Sanders, Samuel N., Oblinsky, Daniel G., Parkin, Sean R., Campos, Luis M., Anthony, John E., and Scholes, Gregory D. Sun . "Photophysical characterization and time-resolved spectroscopy of a anthradithiophene dimer: exploring the role of conformation in singlet fission". United States. doi:10.1039/c7cp03774k.
@article{osti_1535211,
title = {Photophysical characterization and time-resolved spectroscopy of a anthradithiophene dimer: exploring the role of conformation in singlet fission},
author = {Dean, Jacob C. and Zhang, Ruomeng and Hallani, Rawad K. and Pensack, Ryan D. and Sanders, Samuel N. and Oblinsky, Daniel G. and Parkin, Sean R. and Campos, Luis M. and Anthony, John E. and Scholes, Gregory D.},
abstractNote = {We investigate the singlet fission capability of an anthradithiophene dimer.},
doi = {10.1039/c7cp03774k},
journal = {Physical Chemistry Chemical Physics. PCCP (Print)},
issn = {1463-9076},
number = 34,
volume = 19,
place = {United States},
year = {2017},
month = {1}
}

Works referenced in this record:

Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers
journal, October 2006

  • Hanna, M. C.; Nozik, A. J.
  • Journal of Applied Physics, Vol. 100, Issue 7
  • DOI: 10.1063/1.2356795

Detailed Balance Limit of Efficiency of p‐n Junction Solar Cells
journal, March 1961

  • Shockley, William; Queisser, Hans J.
  • Journal of Applied Physics, Vol. 32, Issue 3, p. 510-519
  • DOI: 10.1063/1.1736034

Fission of Entangled Spins: An Electronic Structure Perspective
journal, November 2013

  • Feng, Xintian; Luzanov, Anatoliy V.; Krylov, Anna I.
  • The Journal of Physical Chemistry Letters, Vol. 4, Issue 22
  • DOI: 10.1021/jz402122m

Recent Advances in Singlet Fission
journal, April 2013


A transferable model for singlet-fission kinetics
journal, May 2014

  • Yost, Shane R.; Lee, Jiye; Wilson, Mark W. B.
  • Nature Chemistry, Vol. 6, Issue 6
  • DOI: 10.1038/nchem.1945

The Role of Chromophore Coupling in Singlet Fission
journal, January 2013

  • Johnson, Justin C.; Nozik, Arthur J.; Michl, Josef
  • Accounts of Chemical Research, Vol. 46, Issue 6
  • DOI: 10.1021/ar300193r

Singlet Fission
journal, November 2010

  • Smith, Millicent B.; Michl, Josef
  • Chemical Reviews, Vol. 110, Issue 11
  • DOI: 10.1021/cr1002613

Exciton Delocalization Drives Rapid Singlet Fission in Nanoparticles of Acene Derivatives
journal, May 2015

  • Pensack, Ryan D.; Tilley, Andrew J.; Parkin, Sean R.
  • Journal of the American Chemical Society, Vol. 137, Issue 21
  • DOI: 10.1021/ja512668r

Correlated Pair States Formed by Singlet Fission and Exciton–Exciton Annihilation
journal, December 2015


Observation of Two Triplet-Pair Intermediates in Singlet Exciton Fission
journal, June 2016

  • Pensack, Ryan D.; Ostroumov, Evgeny E.; Tilley, Andrew J.
  • The Journal of Physical Chemistry Letters, Vol. 7, Issue 13
  • DOI: 10.1021/acs.jpclett.6b00947

Toward Designed Singlet Fission: Solution Photophysics of Two Indirectly Coupled Covalent Dimers of 1,3-Diphenylisobenzofuran
journal, November 2012

  • Johnson, Justin C.; Akdag, Akin; Zamadar, Matibur
  • The Journal of Physical Chemistry B, Vol. 117, Issue 16
  • DOI: 10.1021/jp310979q

Mechanism of Singlet Fission in Thin Films of 1,3-Diphenylisobenzofuran
journal, May 2014

  • Schrauben, Joel N.; Ryerson, Joseph L.; Michl, Josef
  • Journal of the American Chemical Society, Vol. 136, Issue 20
  • DOI: 10.1021/ja501337b

An unusual pathway of excitation energy deactivation in carotenoids: Singlet-to-triplet conversion on an ultrafast timescale in a photosynthetic antenna
journal, February 2001

  • Gradinaru, C. C.; Kennis, J. T. M.; Papagiannakis, E.
  • Proceedings of the National Academy of Sciences, Vol. 98, Issue 5
  • DOI: 10.1073/pnas.051501298

Singlet Exciton Fission in Thin Films of tert -Butyl-Substituted Terrylenes
journal, April 2015

  • Eaton, Samuel W.; Miller, Stephen A.; Margulies, Eric A.
  • The Journal of Physical Chemistry A, Vol. 119, Issue 18
  • DOI: 10.1021/acs.jpca.5b02719

Enabling singlet fission by controlling intramolecular charge transfer in π-stacked covalent terrylenediimide dimers
journal, August 2016

  • Margulies, Eric A.; Miller, Claire E.; Wu, Yilei
  • Nature Chemistry, Vol. 8, Issue 12
  • DOI: 10.1038/nchem.2589

A design strategy for intramolecular singlet fission mediated by charge-transfer states in donor–acceptor organic materials
journal, January 2015

  • Busby, Erik; Xia, Jianlong; Wu, Qin
  • Nature Materials, Vol. 14, Issue 4
  • DOI: 10.1038/nmat4175

Singlet Fission via an Excimer-Like Intermediate in 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives
journal, August 2016

  • Mauck, Catherine M.; Hartnett, Patrick E.; Margulies, Eric A.
  • Journal of the American Chemical Society, Vol. 138, Issue 36
  • DOI: 10.1021/jacs.6b05627

Singlet exciton fission in solution
journal, November 2013

  • Walker, Brian J.; Musser, Andrew J.; Beljonne, David
  • Nature Chemistry, Vol. 5, Issue 12
  • DOI: 10.1038/nchem.1801

Ultrafast Dynamics of Exciton Fission in Polycrystalline Pentacene
journal, August 2011

  • Wilson, Mark W. B.; Rao, Akshay; Clark, Jenny
  • Journal of the American Chemical Society, Vol. 133, Issue 31
  • DOI: 10.1021/ja201688h

Singlet Fission in Polypentacene
journal, September 2016


Aqueous Colloidal Acene Nanoparticles: A New Platform for Studying Singlet Fission
journal, July 2013

  • Mastron, Joseph N.; Roberts, Sean T.; McAnally, R. Eric
  • The Journal of Physical Chemistry B, Vol. 117, Issue 49
  • DOI: 10.1021/jp4057972

Tuneable Singlet Exciton Fission and Triplet-Triplet Annihilation in an Orthogonal Pentacene Dimer
journal, August 2015

  • Lukman, Steven; Musser, Andrew J.; Chen, Kai
  • Advanced Functional Materials, Vol. 25, Issue 34
  • DOI: 10.1002/adfm.201501537

Singlet fission in pentacene dimers
journal, April 2015

  • Zirzlmeier, Johannes; Lehnherr, Dan; Coto, Pedro B.
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 17
  • DOI: 10.1073/pnas.1422436112

Quantitative Intramolecular Singlet Fission in Bipentacenes
journal, July 2015

  • Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B.
  • Journal of the American Chemical Society, Vol. 137, Issue 28
  • DOI: 10.1021/jacs.5b04986

Functionalized Acenes and Heteroacenes for Organic Electronics
journal, December 2006


Exciton Correlations in Intramolecular Singlet Fission
journal, June 2016

  • Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B.
  • Journal of the American Chemical Society, Vol. 138, Issue 23
  • DOI: 10.1021/jacs.6b00657

Intramolecular Singlet Fission in Oligoacene Heterodimers
journal, February 2016

  • Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B.
  • Angewandte Chemie International Edition, Vol. 55, Issue 10
  • DOI: 10.1002/anie.201510632

Singlet Fission in a Covalently Linked Cofacial Alkynyltetracene Dimer
journal, January 2016

  • Korovina, Nadezhda V.; Das, Saptaparna; Nett, Zachary
  • Journal of the American Chemical Society, Vol. 138, Issue 2
  • DOI: 10.1021/jacs.5b10550

Synthesis and photophysical properties of a “face-to-face” stacked tetracene dimer
journal, January 2015

  • Liu, Heyuan; Nichols, Valerie M.; Shen, Li
  • Physical Chemistry Chemical Physics, Vol. 17, Issue 9
  • DOI: 10.1039/C4CP05444J

Excimer Formation in van der Waals Dimers and Clusters of Aromatic Molecules
journal, January 1996

  • Saigusa, Hiroyuki; Lim, Edward C.
  • Accounts of Chemical Research, Vol. 29, Issue 4
  • DOI: 10.1021/ar950169v

Excimer geometries in bichromophoric molecules: A theoretical and experimental study of 1,2-(bis-9-anthryl)-ethane
journal, August 1991


Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized media
journal, March 1993


Synthesis, Morphology, and Field-Effect Mobility of Anthradithiophenes
journal, February 1998

  • Laquindanum, Joyce G.; Katz, Howard E.; Lovinger, Andrew J.
  • Journal of the American Chemical Society, Vol. 120, Issue 4
  • DOI: 10.1021/ja9728381

Optical, Fluorescent, and (Photo)conductive Properties of High-Performance Functionalized Pentacene and Anthradithiophene Derivatives
journal, July 2009

  • Platt, Andrew D.; Day, Jonathan; Subramanian, Sankar
  • The Journal of Physical Chemistry C, Vol. 113, Issue 31
  • DOI: 10.1021/jp904021p

Excessive Exoergicity Reduces Singlet Exciton Fission Efficiency of Heteroacenes in Solutions
journal, May 2016

  • Zhang, You-Dan; Wu, Yishi; Xu, Yanqing
  • Journal of the American Chemical Society, Vol. 138, Issue 21
  • DOI: 10.1021/jacs.6b03829

Effects of Heteroatoms of Tetracene and Pentacene Derivatives on Their Stability and Singlet Fission
journal, July 2014

  • Chen, Yuhan; Shen, Li; Li, Xiyou
  • The Journal of Physical Chemistry A, Vol. 118, Issue 30
  • DOI: 10.1021/jp503114b

Structural and Electronic Properties of Crystalline, Isomerically Pure Anthradithiophene Derivatives
journal, November 2015

  • Hallani, Rawad K.; Thorley, Karl J.; Mei, Yaochuan
  • Advanced Functional Materials, Vol. 26, Issue 14
  • DOI: 10.1002/adfm.201502440

Glotaran : A Java -Based Graphical User Interface for the R Package TIMP
journal, January 2012

  • Snellenburg, Joris J.; Laptenok, Sergey P.; Seger, Ralf
  • Journal of Statistical Software, Vol. 49, Issue 3
  • DOI: 10.18637/jss.v049.i03

A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP)
journal, July 2004

  • Yanai, Takeshi; Tew, David P.; Handy, Nicholas C.
  • Chemical Physics Letters, Vol. 393, Issue 1-3, p. 51-57
  • DOI: 10.1016/j.cplett.2004.06.011

Multiphonon Relaxation Slows Singlet Fission in Crystalline Hexacene
journal, July 2014

  • Busby, Erik; Berkelbach, Timothy C.; Kumar, Bharat
  • Journal of the American Chemical Society, Vol. 136, Issue 30
  • DOI: 10.1021/ja503980c

Real-time observation of multiexcitonic states in ultrafast singlet fission using coherent 2D electronic spectroscopy
journal, October 2015

  • Bakulin, Artem A.; Morgan, Sarah E.; Kehoe, Tom B.
  • Nature Chemistry, Vol. 8, Issue 1
  • DOI: 10.1038/nchem.2371

Role of Intermolecular Coupling in the Photophysics of Disordered Organic Semiconductors: Aggregate Emission in Regioregular Polythiophene
journal, May 2007


The Spectral Signatures of Frenkel Polarons in H- and J-Aggregates
journal, March 2010

  • Spano, Frank C.
  • Accounts of Chemical Research, Vol. 43, Issue 3
  • DOI: 10.1021/ar900233v

Broadband Transient Absorption and Two-Dimensional Electronic Spectroscopy of Methylene Blue
journal, August 2015

  • Dean, Jacob C.; Rafiq, Shahnawaz; Oblinsky, Daniel G.
  • The Journal of Physical Chemistry A, Vol. 119, Issue 34
  • DOI: 10.1021/acs.jpca.5b06126

Direct Observation of Ultrafast Excimer Formation in Covalent Perylenediimide Dimers Using Near-Infrared Transient Absorption Spectroscopy
journal, July 2014

  • Brown, Kristen E.; Salamant, Walter A.; Shoer, Leah E.
  • The Journal of Physical Chemistry Letters, Vol. 5, Issue 15
  • DOI: 10.1021/jz5011797

Excited Singlet States of Covalently Bound, Cofacial Dimers and Trimers of Perylene-3,4:9,10-bis(dicarboximide)s
journal, March 2008

  • Giaimo, Jovan M.; Lockard, Jenny V.; Sinks, Louise E.
  • The Journal of Physical Chemistry A, Vol. 112, Issue 11
  • DOI: 10.1021/jp710847q

Energy transfer and spectroscopic characterization of a perylenetetracarboxylic diimide (PDI) hexamer
journal, January 2015

  • Long, Saran; Wang, Yingying; Vdović, Silvije
  • Physical Chemistry Chemical Physics, Vol. 17, Issue 28
  • DOI: 10.1039/C5CP01514F

First Experimental Evidence for the Diverse Requirements of Excimer vs Hole Stabilization in π-Stacked Assemblies
journal, July 2016

  • Reilly, Neil; Ivanov, Maxim; Uhler, Brandon
  • The Journal of Physical Chemistry Letters, Vol. 7, Issue 15
  • DOI: 10.1021/acs.jpclett.6b01201