A molecular plug - socket connector
— Northwestern Scholars Skip to main navigation Skip to search Skip to main content Help & FAQ Home Experts Organizations Research Output Grants Core Facilities Search by expertise, name or affiliation A molecular plug - socket connector Guillaume Rogez, Belén Ferrer Ribera, Alberto Credi*, Roberto Ballardini, Maria Teresa Gandolfi, Vincenzo Balzani, Yi Liu, Brian H. Northrop, J. Fraser Stoddart *Corresponding author for this work Chemistry Research output: Contribution to journal › Article › peer-review 46 Scopus citations Overview Fingerprint Abstract A monocationic plug-socket connector that is composed, at the molecular level, of three components, (1) a secondary dialkylammonium center (CH 2NH2+CH2), which can play the role of a plug toward dibenzo[24]crown-8 (DB24C8), (2) a rigid and conducting biphenyl spacer, and (3) 1,4-benzo-1,5-naphtho[36]crown-10 (BN36C10), capable of playing the role of a socket toward a 4,4′-bipyridinium dicationic plug, was synthesized and displays the ability to act as a plug-socket connector. The fluorescent signal changes associated with the 1,5-dioxynaphthalene unit of its BN36C10 portion were monitored to investigate the association of this plug-socket connector with the complementary socket and plug compounds. The results indicate that (1) the CH2NH2+CH 2 part of the molecular connector can thread DB24C8 in a trivial manner and (2) the BN36C10 ring of the connector can be threaded by a 1,1′-dioctyl-4,4′-bipyridinium ion only after the CH 2NH2+CH2 site is occupied by a DB24C8 ring. The two connections of the three-component assembly are shown to be controlled reversibly by acid/base and red/ox external inputs, respectively. The results obtained represent a key step for the design and construction of a self-assembling supramolecular system in which the molecular electron source can be connected to the molecular electron drain by a molecular elongation cable. Original language English (US) Pages (from-to) 4633-4642 Number of pages 10 Journal Journal of the American Chemical Society Volume 129 Issue number 15 DOIs https://doi.org/10.1021/ja067739e State Published - Apr 18 2007 ASJC Scopus subject areas Catalysis Chemistry(all) Biochemistry Colloid and Surface Chemistry Access to Document 10.1021/ja067739e Link to publication in Scopus Link to citation list in Scopus Fingerprint Dive into the research topics of 'A molecular plug - socket connector'. Together they form a unique fingerprint. Electron sources Engineering & Materials Science Crowns Medicine & Life Sciences Electrons Engineering & Materials Science Elongation Engineering & Materials Science Ions Engineering & Materials Science Acids Engineering & Materials Science Cables Engineering & Materials Science lissamine rhodamine B Medicine & Life Sciences View full fingerprint Cite this APA Author BIBTEX Harvard Standard RIS Vancouver Rogez, G., Ribera, B. F., Credi, A., Ballardini, R., Gandolfi, M. T., Balzani, V., Liu, Y., Northrop, B. H., & Stoddart, J. F. (2007). A molecular plug - socket connector. Journal of the American Chemical Society, 129(15), 4633-4642. https://doi.org/10.1021/ja067739e Rogez, Guillaume ; Ribera, Belén Ferrer ; Credi, Alberto ; Ballardini, Roberto ; Gandolfi, Maria Teresa ; Balzani, Vincenzo ; Liu, Yi ; Northrop, Brian H. ; Stoddart, J. Fraser. / A molecular plug - socket connector. In: Journal of the American Chemical Society. 2007 ; Vol. 129, No. 15. pp. 4633-4642. @article{9a2e75e7b001406bb0974afc47011a87, title = "A molecular plug - socket connector", abstract = "A monocationic plug-socket connector that is composed, at the molecular level, of three components, (1) a secondary dialkylammonium center (CH 2NH2+CH2), which can play the role of a plug toward dibenzo[24]crown-8 (DB24C8), (2) a rigid and conducting biphenyl spacer, and (3) 1,4-benzo-1,5-naphtho[36]crown-10 (BN36C10), capable of playing the role of a socket toward a 4,4′-bipyridinium dicationic plug, was synthesized and displays the ability to act as a plug-socket connector. The fluorescent signal changes associated with the 1,5-dioxynaphthalene unit of its BN36C10 portion were monitored to investigate the association of this plug-socket connector with the complementary socket and plug compounds. The results indicate that (1) the CH2NH2+CH 2 part of the molecular connector can thread DB24C8 in a trivial manner and (2) the BN36C10 ring of the connector can be threaded by a 1,1′-dioctyl-4,4′-bipyridinium ion only after the CH 2NH2+CH2 site is occupied by a DB24C8 ring. The two connections of the three-component assembly are shown to be controlled reversibly by acid/base and red/ox external inputs, respectively. The results obtained represent a key step for the design and construction of a self-assembling supramolecular system in which the molecular electron source can be connected to the molecular electron drain by a molecular elongation cable.", author = "Guillaume Rogez and Ribera, {Bel{\'e}n Ferrer} and Alberto Credi and Roberto Ballardini and Gandolfi, {Maria Teresa} and Vincenzo Balzani and Yi Liu and Northrop, {Brian H.} and Stoddart, {J. Fraser}", year = "2007", month = apr, day = "18", doi = "10.1021/ja067739e", language = "English (US)", volume = "129", pages = "4633--4642", journal = "Journal of the American Chemical Society", issn = "0002-7863", publisher = "American Chemical Society", number = "15", } Rogez, G, Ribera, BF, Credi, A, Ballardini, R, Gandolfi, MT, Balzani, V, Liu, Y, Northrop, BH & Stoddart, JF 2007, 'A molecular plug - socket connector', Journal of the American Chemical Society, vol. 129, no. 15, pp. 4633-4642. https://doi.org/10.1021/ja067739e A molecular plug - socket connector. / Rogez, Guillaume; Ribera, Belén Ferrer; Credi, Alberto; Ballardini, Roberto; Gandolfi, Maria Teresa; Balzani, Vincenzo; Liu, Yi; Northrop, Brian H.; Stoddart, J. Fraser. In: Journal of the American Chemical Society, Vol. 129, No. 15, 18.04.2007, p. 4633-4642. Research output: Contribution to journal › Article › peer-review TY - JOUR T1 - A molecular plug - socket connector AU - Rogez, Guillaume AU - Ribera, Belén Ferrer AU - Credi, Alberto AU - Ballardini, Roberto AU - Gandolfi, Maria Teresa AU - Balzani, Vincenzo AU - Liu, Yi AU - Northrop, Brian H. AU - Stoddart, J. Fraser PY - 2007/4/18 Y1 - 2007/4/18 N2 - A monocationic plug-socket connector that is composed, at the molecular level, of three components, (1) a secondary dialkylammonium center (CH 2NH2+CH2), which can play the role of a plug toward dibenzo[24]crown-8 (DB24C8), (2) a rigid and conducting biphenyl spacer, and (3) 1,4-benzo-1,5-naphtho[36]crown-10 (BN36C10), capable of playing the role of a socket toward a 4,4′-bipyridinium dicationic plug, was synthesized and displays the ability to act as a plug-socket connector. The fluorescent signal changes associated with the 1,5-dioxynaphthalene unit of its BN36C10 portion were monitored to investigate the association of this plug-socket connector with the complementary socket and plug compounds. The results indicate that (1) the CH2NH2+CH 2 part of the molecular connector can thread DB24C8 in a trivial manner and (2) the BN36C10 ring of the connector can be threaded by a 1,1′-dioctyl-4,4′-bipyridinium ion only after the CH 2NH2+CH2 site is occupied by a DB24C8 ring. The two connections of the three-component assembly are shown to be controlled reversibly by acid/base and red/ox external inputs, respectively. The results obtained represent a key step for the design and construction of a self-assembling supramolecular system in which the molecular electron source can be connected to the molecular electron drain by a molecular elongation cable. AB - A monocationic plug-socket connector that is composed, at the molecular level, of three components, (1) a secondary dialkylammonium center (CH 2NH2+CH2), which can play the role of a plug toward dibenzo[24]crown-8 (DB24C8), (2) a rigid and conducting biphenyl spacer, and (3) 1,4-benzo-1,5-naphtho[36]crown-10 (BN36C10), capable of playing the role of a socket toward a 4,4′-bipyridinium dicationic plug, was synthesized and displays the ability to act as a plug-socket connector. The fluorescent signal changes associated with the 1,5-dioxynaphthalene unit of its BN36C10 portion were monitored to investigate the association of this plug-socket connector with the complementary socket and plug compounds. The results indicate that (1) the CH2NH2+CH 2 part of the molecular connector can thread DB24C8 in a trivial manner and (2) the BN36C10 ring of the connector can be threaded by a 1,1′-dioctyl-4,4′-bipyridinium ion only after the CH 2NH2+CH2 site is occupied by a DB24C8 ring. The two connections of the three-component assembly are shown to be controlled reversibly by acid/base and red/ox external inputs, respectively. The results obtained represent a key step for the design and construction of a self-assembling supramolecular system in which the molecular electron source can be connected to the molecular electron drain by a molecular elongation cable. UR - http://www.scopus.com/inward/record.url?scp=34247505509&partnerID=8YFLogxK UR - http://www.scopus.com/inward/citedby.url?scp=34247505509&partnerID=8YFLogxK U2 - 10.1021/ja067739e DO - 10.1021/ja067739e M3 - Article C2 - 17388589 AN - SCOPUS:34247505509 VL - 129 SP - 4633 EP - 4642 JO - Journal of the American Chemical Society JF - Journal of the American Chemical Society SN - 0002-7863 IS - 15 ER - Rogez G, Ribera BF, Credi A, Ballardini R, Gandolfi MT, Balzani V et al. A molecular plug - socket connector. Journal of the American Chemical Society. 2007 Apr 18;129(15):4633-4642. https://doi.org/10.1021/ja067739e Powered by Pure, Scopus & Elsevier Fingerprint Engine™ © 2021 Elsevier B.V "We use cookies to help provide and enhance our service and tailor content. By continuing you agree to the use of cookies Log in to Pure About web accessibility Northwestern Scholars contact form
