Fluorescence-Lifetime Imaging and Super-Resolution Microscopies Shed Light on the Directed- and Self-Assembly of Functional Porphyrins onto Carbon Nanotubes and Flat Surfaces.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 9513783 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3765 (Electronic) Linking ISSN: 09476539 NLM ISO Abbreviation: Chemistry Subsets: PubMed not MEDLINE

Original Publication: Weinheim, Germany : Wiley-VCH

Functional porphyrins have attracted intense attention due to their remarkably high extinction coefficients in the visible region and potential for optical and energy-related applications. Two new routes to functionalised SWNTs have been established using a bulky Zn ^II -porphyrin featuring thiolate groups at the periphery. We probed the optical properties of this zinc(II)-substituted, bulky aryl porphyrin and those of the corresponding new nano-composites with single walled carbon nanotube (SWNTs) and coronene, as a model for graphene. We report hereby on: i) the supramolecular interactions between the pristine SWNTs and Zn ^II -porphyrin by virtue of π-π stacking, and ii) a novel covalent binding strategy based on the Bingel reaction. The functional porphyrins used acted as dispersing agent for the SWNTs and the resulting nanohybrids showed improved dispersibility in common organic solvents. The synthesized hybrid materials were probed by various characterisation techniques, leading to the prediction that supramolecular polymerisation and host-guest functionalities control the fluorescence emission intensity and fluorescence lifetime properties. For the first time, XPS studies highlighted the differences in covalent versus non-covalent attachments of functional metalloporphyrins to SWNTs. Gas-phase DFT calculations indicated that the Zn ^II -porphyrin interacts non-covalently with SWNTs to form a donor-acceptor complex. The covalent attachment of the porphyrin chromophore to the surface of SWNTs affects the absorption and emission properties of the hybrid system to a greater extent than in the case of the supramolecular functionalisation of the SWNTs. This represents a synthetic challenge as well as an opportunity in the design of functional nanohybrids for future sensing and optoelectronic applications.
(© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Chemistry. 2008;14(10):3035-44. (PMID: 18293350)
Angew Chem Int Ed Engl. 2015 Jun 15;54(25):7344-8. (PMID: 25950655)
Langmuir. 2005 Jun 21;21(13):6086-92. (PMID: 15952864)
Angew Chem Int Ed Engl. 2005 Mar 18;44(13):2015-8. (PMID: 15724261)
Chem Soc Rev. 2009 Jan;38(1):165-84. (PMID: 19088972)
Nature. 2017 Jan 12;541(7636):200-203. (PMID: 27992878)
Chemistry. 2008;14(29):8837-46. (PMID: 18767110)
Langmuir. 2004 Oct 26;20(22):9807-10. (PMID: 15491218)
Angew Chem Weinheim Bergstr Ger. 2015 Apr 27;127(18):5445-5449. (PMID: 27546919)
J Am Chem Soc. 2003 Jul 23;125(29):8722-3. (PMID: 12862456)
Science. 2002 Aug 2;297(5582):787-92. (PMID: 12161643)
Phys Chem Chem Phys. 2013 Sep 28;15(36):14896-918. (PMID: 23913009)
J Phys Chem B. 2006 Dec 28;110(51):26068-74. (PMID: 17181259)
Phys Rev Lett. 1996 Oct 28;77(18):3865-3868. (PMID: 10062328)
Nano Lett. 2007 Mar;7(3):676-80. (PMID: 17309316)
J Nanosci Nanotechnol. 2007 Apr-May;7(4-5):1530-8. (PMID: 17450922)
J Am Chem Soc. 2005 Jun 8;127(22):8197-203. (PMID: 15926849)
Chem Soc Rev. 2015 Jul 7;44(13):4239-4248. (PMID: 25474366)
J Am Chem Soc. 2006 Sep 27;128(38):12544-52. (PMID: 16984205)
J Am Chem Soc. 2005 Aug 31;127(34):11884-5. (PMID: 16117495)
Angew Chem Int Ed Engl. 2002 Jun 3;41(11):1853-9. (PMID: 19750614)
J Am Chem Soc. 2011 Nov 2;133(43):17262-73. (PMID: 21939246)
J Phys Chem Lett. 2014 Dec 18;5(24):4356-61. (PMID: 26273987)
Chemistry. 2017 Jul 21;23(41):9772-9789. (PMID: 28444700)
J Am Chem Soc. 2007 Apr 4;129(13):3938-45. (PMID: 17343379)
J Comput Chem. 2006 Nov 30;27(15):1787-99. (PMID: 16955487)
Chemistry. 2004 Feb 20;10(4):812-7. (PMID: 14978808)
Nano Lett. 2006 Sep;6(9):2031-6. (PMID: 16968021)
Angew Chem Int Ed Engl. 2004 Oct 18;43(41):5526-30. (PMID: 15484237)
Angew Chem Weinheim Bergstr Ger. 2015 Jun 15;127(25):7452-7456. (PMID: 27478266)
Acc Chem Res. 2002 Dec;35(12):1105-13. (PMID: 12484799)
Angew Chem Int Ed Engl. 2014 Feb 17;53(8):2170-5. (PMID: 24453140)
J Am Chem Soc. 2005 Aug 3;127(30):10731-8. (PMID: 16045362)
J Am Chem Soc. 2013 Apr 24;135(16):6372-7. (PMID: 23570612)
Chem Soc Rev. 2007 Feb;36(2):161-71. (PMID: 17264920)
J Am Chem Soc. 2006 Aug 30;128(34):11222-31. (PMID: 16925441)
J Am Chem Soc. 2009 Oct 28;131(42):15394-402. (PMID: 19919163)
Adv Mater. 2016 Nov;28(44):9668-9685. (PMID: 27633954)
J Am Chem Soc. 2006 May 24;128(20):6626-35. (PMID: 16704263)
Dalton Trans. 2011 Nov 7;40(41):10833-42. (PMID: 21779604)
Nat Nanotechnol. 2017 May;12(4):368-377. (PMID: 28114298)
J Phys Chem B. 2006 Dec 21;110(50):25477-84. (PMID: 17165996)
Acc Chem Res. 2005 Nov;38(11):871-8. (PMID: 16285709)
Chem Soc Rev. 2006 May;35(5):471-87. (PMID: 16636729)
Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5355-9. (PMID: 25683453)
Angew Chem Int Ed Engl. 2006 Jun 2;45(23):3779-81. (PMID: 16671138)

Keywords: carbon nanotubes; nanostructures; optically active materials; self-assembly; super-resolution STED imaging

Date Created: 20170427 Date Completed: 20180131 Latest Revision: 20210109

20231215

PMC5724654

10.1002/chem.201605232

28444700