Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH15196
RESEARCH FRONT
Contents Vol 68(9)

Enhanced Squaraine Rotaxane Endoperoxide Chemiluminescence in Acidic Alcohols

Evan M. Peck A , Allen G. Oliver A and Bradley D. Smith A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry and Biochemistry, 236 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556, USA.

B Corresponding author. Email: smith.115@nd.edu

Australian Journal of Chemistry 68(9) 1359-1364 https://doi.org/10.1071/CH15196
Submitted: 17 April 2015  Accepted: 30 April 2015   Published: 27 May 2015

Abstract

Squaraine rotaxane endoperoxides (SREPs) are storable chemiluminescent compounds that undergo a clean cycloreversion reaction that releases singlet oxygen and emits near-infrared light when warmed to body temperature. This study examined the effect of solvent on SREP chemiluminescence intensity and found that acidic alcohols, such as 2,2,2-trifluoroethanol, α-(trifluoromethyl)benzyl alcohol, and 1,1,1,3,3,3-hexafluoroisopropanol, greatly increased chemiluminescence. In contrast, aprotic solvents, such as trifluoroethylmethyl ether, had no effect. The interlocked rotaxane structure was necessary as no chemiluminescence was observed when the experiments were conducted with samples containing a mixture of the two non-interlocked components (squaraine thread and macrocycle endoperoxide). Spectroscopic analyses of the enhanced SREP chemiluminescent reactions showed a mixture of products. In addition to the expected squaraine rotaxane product caused by cycloreversion of the endoperoxide, a diol derivative was isolated. The results are consistent with an endoperoxide O–O bond cleavage process that is promoted by the hydrogen bonding solvent and produces light emission from a squaraine excited state.


References

[1]  E. A. Neal, S. M. Goldup, Chem. Commun. 2014, 50, 5128.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmsFCjs78%3D&md5=819ab22241e0a0748bd5da49156585f4CAS |

[2]  E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem., Int. Ed. 2007, 46, 72.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXitlCqtQ%3D%3D&md5=8b5800734047b93fe58017f8e3b1797eCAS |

[3]  D. A. Leigh, P. J. Lusby, A. M. Z. Slawin, D. B. Walker, Angew. Chem., Int. Ed. 2005, 44, 4557.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXntVSgtrw%3D&md5=42793d829a29275ea080b1acaafd8e29CAS |

[4]  W. R. Browne, B. L. Feringa, Nat. Nanotechnol. 2006, 1, 25.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFCisr3F&md5=7c83790cdc17062997699b39d34839b3CAS | 18654138PubMed |

[5]  J.-M. Lehn, Chem. Soc. Rev. 2007, 36, 151.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVKlu74%3D&md5=f36130b866c810fd8d02bb68c955a226CAS | 17264919PubMed |

[6]  R. Klajn, J. F. Stoddart, B. A. Grzybowski, Chem. Soc. Rev. 2010, 39, 2203.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmsFertr4%3D&md5=4b331d98513aac5ade25ae33e645ba3aCAS | 20407689PubMed |

[7]  H. Li, Z. Zhu, A. C. Fahrenbach, B. M. Savoie, C. Ke, J. C. Barnes, J. Lei, Y.-L. Zhao, L. M. Lilley, T. J. Marks, M. A. Ratner, J. F. Stoddart, J. Am. Chem. Soc. 2013, 135, 456.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhs12mtL%2FI&md5=196e2fc554c20deda2dc71b8c57137aaCAS | 23163704PubMed |

[8]  A. Fernandes, A. Viterisi, F. Coutrot, S. Potok, D. A. Leigh, V. Aucagne, S. Papot, Angew. Chem., Int. Ed. 2009, 121, 6565.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  E. Arunkumar, C. C. Forbes, B. C. Noll, B. D. Smith, J. Am. Chem. Soc. 2005, 127, 3288.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtl2ntr0%3D&md5=a6d72ca14d844c7908be7839991db3b7CAS | 15755140PubMed |

[10]  M. R. Craig, M. G. Hutchings, T. D. W. Claridge, H. L. Anderson, Angew. Chem., Int. Ed. 2001, 40, 1071.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXisVCiu7Y%3D&md5=147e3d6a7a7a68bc401fb95135a0bc12CAS |

[11]  J. E. H. Buston, J. R. Young, H. L. Anderson, Chem. Commun. 2000, 905.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjsFSltLc%3D&md5=94562283473c577c90894f548b92db13CAS |

[12]  T. Oku, Y. Furusho, T. Takata, Org. Lett. 2003, 5, 4923.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpt1ajsrg%3D&md5=f43ac04c5f1fe14f6b0b266e8682da54CAS | 14682730PubMed |

[13]  C. B. Caputo, K. Zhu, V. N. Vukotic, S. J. Loeb, D. W. Stephan, Angew. Chem., Int. Ed. 2013, 52, 960.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslejtLjE&md5=088cb5148bde556d961b628c8b79febbCAS |

[14]  Y. Suzaki, K. Shimada, E. Chihara, T. Saito, Y. Tsuchido, K. Osakada, Org. Lett. 2011, 13, 3774.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXotFSnu74%3D&md5=d55c17579ed2c33c5620fd8f5d398ea5CAS | 21711007PubMed |

[15]  J. Berná, M. Alajarín, R.-A. Orenes, J. Am. Chem. Soc. 2010, 132, 10741.
         | Crossref | GoogleScholarGoogle Scholar | 20681706PubMed |

[16]  D. M. D’Souza, D. A. Leigh, L. Mottier, K. M. Mullen, F. Paolucci, S. J. Teat, S. Zhang, J. Am. Chem. Soc. 2010, 132, 9465.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnsFyhtbk%3D&md5=c78cdb67fe92b70f6268bcf2342a9230CAS | 20552981PubMed |

[17]  J. M. Baumes, J. J. Gassensmith, J. Giblin, J.-J. Lee, A. G. White, W. J. Culligan, W. M. Leevy, M. Kuno, B. D. Smith, Nat. Chem. 2010, 2, 1025.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVOrsL3I&md5=552dead8ce5f4daf15725c09c7cbc643CAS | 21107365PubMed |

[18]  J. M. Baumes, I. Murgu, A. Oliver, B. D. Smith, Org. Lett. 2010, 12, 4980.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1Cgs7jJ&md5=9923caa52e50799b099f7a59a9659be7CAS | 20923203PubMed |

[19]  K. Cui, X. Xu, H. Zhao, S. T. C. Wong, Luminescence 2008, 23, 292.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlahu7bO&md5=23913e5beaf71a438350a4be37af1fa2CAS | 18452141PubMed |

[20]  J. A. Prescher, C. H. Contag, Curr. Opin. Chem. Biol. 2010, 14, 80.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht12qtL0%3D&md5=81cf8c96ff61c6372119319f42a6c330CAS | 19962933PubMed |

[21]  A. Roda, M. Guardigli, E. Michelini, M. Mirasoli, TrAC, Trends Anal. Chem. 2009, 28, 307.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXitlGnu7o%3D&md5=099f9a8f2e05380c5a40fdb3832b805fCAS |

[22]  K. A. Zaklika, P. A. Burns, A. P. Schaap, J. Am. Chem. Soc. 1978, 100, 318.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1cXhsFWktr0%3D&md5=cbe24801e444a35917056ac2438efaaeCAS |

[23]  K. A. Zaklika, T. Kissel, A. L. Thayer, P. A. Burns, A. P. Schaap, Photochem. Photobiol. 1979, 30, 35.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXhvFOltLY%3D&md5=d149c031c137904f31b32b0676bf7ec2CAS |

[24]  I. Bronstein, B. Edwards, J. C. Voyta, J. Biolumin. Chemilumin. 1989, 4, 99.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXmt1Olsbo%3D&md5=30ab8bb3dfcbb59aa450a9c0477c093bCAS | 2477995PubMed |

[25]  C. G. Collins, J. M. Lee, A. G. Oliver, O. Wiest, B. D. Smith, J. Org. Chem. 2014, 79, 1120.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXotVeqtA%3D%3D&md5=bbf91939df3b9fcd6eda1f8da5cbea40CAS | 24428682PubMed |

[26]  J. J. Gassensmith, L. Barr, J. M. Baumes, A. Paek, A. Nguyen, B. D. Smith, Org. Lett. 2008, 10, 3343.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXnvF2hurw%3D&md5=e4661d7e655ca58c5da91ccb39bb7da5CAS | 18582079PubMed |

[27]  D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawain, Angew. Chem., Int. Ed. Engl. 1997, 36, 728.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXjtVajtrY%3D&md5=b2b97068d6d2b74f029750aa6fc6d01cCAS |

[28]  J. J. Gassensmith, E. Arunkumar, L. Barr, J. M. Baumes, K. M. DiVittorio, J. R. Johnson, B. C. Noll, B. D. Smith, J. Am. Chem. Soc. 2007, 129, 15054.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht12gsrfL&md5=169d19bf949968f8d32718702a7fbdc6CAS | 17994746PubMed |

[29]  J. J. Gassensmith, J. M. Baumes, B. D. Smith, Chem. Commun. 2009, 6329.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1yisrbM&md5=0b4af2b59bcc86410e14d6311cc823daCAS |

[30]  N. Fu, J. M. Baumes, E. Arunkumar, B. C. Noll, B. D. Smith, J. Org. Chem. 2009, 74, 6462.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXptFChsbw%3D&md5=e17da01cc352a03cfa1d36a8a5d68942CAS | 19639940PubMed |

[31]  J.-M. Aubry, C. Pierlot, J. Rigaudy, R. Schmidt, Acc. Chem. Res. 2003, 36, 668.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXltF2rs7s%3D&md5=5b21ba2010b24b40084f012d124df05aCAS | 12974650PubMed |

[32]  R. L. Donkers, M. S. Workentin, J. Am. Chem. Soc. 2004, 126, 1688.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmtFSksw%3D%3D&md5=577b0c4e4ecc2ddade4b0a39249bde0bCAS | 14871099PubMed |

[33]  P. Salice, J. Arnbjerg, B. W. Pedersen, R. Toftegaard, L. Beverina, G. A. Pagani, P. R. Ogilby, J. Phys. Chem. A 2010, 114, 2518.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlCgsLY%3D&md5=3075648a8fc403837cdbe7b78dbdfbe8CAS | 20121177PubMed |

[34]  M. Matsumoto, J. Photochem. Photobiol. Chem. 2004, 5, 27.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjvVGjsrY%3D&md5=4956b467f646ed0d1304e00845928cc3CAS |

[35]  S. Xiao, N. Fu, K. Peckham, B. D. Smith, Org. Lett. 2009, 12, 14.

[36]  G. M. Sheldrick, Acta Crystallogr. Sect. A: Found. Crystallogr. 2008, 64, 112.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVGhurzO&md5=59f548f8f29686b585f885edea91b42eCAS |