Towards Molecular Design Rationalization in Branched Multi-Thiophene Semiconductors: The 2-Thienyl-Persubstituted α-Oligothiophenes

The introduction of branching in multi‐thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering π conjugation. Accordingly, branched oligothiophenes require rationalization of t...

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Published inChemistry : a European journal Vol. 16; no. 30; pp. 9086 - 9098
Main Authors Benincori, Tiziana, Bonometti, Valentina, De Angelis, Filippo, Falciola, Luigi, Muccini, Michele, Mussini, Patrizia R., Pilati, Tullio, Rampinini, Giovanni, Rizzo, Simona, Toffanin, Stefano, Sannicolò, Francesco
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 09.08.2010
WILEY‐VCH Verlag
Wiley
Subjects
Accessibility
Branched
Chains
Chemistry
Chemistry, Multidisciplinary
conducting materials
conjugation
dendrimers
Design engineering
oligothiophenes
Physical Sciences
Polymerization
Science & Technology
Semiconductors
Spectroscopy
structure-activity relationships
Thiophenes
POLYMERS
SERIES
dendrimers
SELENOPHENES
conducting materials
POTENTIALS
MODEL
conjugation
structure-activity relationships
RECOMMENDATIONS
NONAQUEOUS SOLVENTS
ENERGY-TRANSFER
oligothiophenes
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Abstract The introduction of branching in multi‐thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering π conjugation. Accordingly, branched oligothiophenes require rationalization of their structure–reactivity relationships for target‐oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T′XY, of five new multi‐thiophene systems, T′53, T′84, T′115, T′146, and T′177, constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest α‐conjugated chain consisting of tri‐, tetra‐, penta‐, hexa‐, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5‐(2,2′‐dithiophene)yl‐persubstituted α‐oligothiophenes (TXY) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells. Branching out: A series of multi‐thiophene systems comprising 5, 8, 11, 14, and 17 thiophene units (an example of which is depicted), their longest α‐conjugated chain consisting of tri‐, tetra‐, penta‐, hexa‐, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view.
AbstractList The introduction of branching in multi-thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering pi conjugation. Accordingly, branched oligothiophenes require rationalization of their structure-reactivity relationships for target-oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T'X(Y), of five new multi-thiophene systems, T'5(3), T'8(4), T'11(5), T'14(6), and T'17(7), constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest alpha-conjugated chain consisting of tri-, tetra-, penta-, hexa-, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5-(2,2'-dithiophene)yl-persubstituted alpha-oligothiophenes (TX(Y)) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells.The introduction of branching in multi-thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering pi conjugation. Accordingly, branched oligothiophenes require rationalization of their structure-reactivity relationships for target-oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T'X(Y), of five new multi-thiophene systems, T'5(3), T'8(4), T'11(5), T'14(6), and T'17(7), constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest alpha-conjugated chain consisting of tri-, tetra-, penta-, hexa-, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5-(2,2'-dithiophene)yl-persubstituted alpha-oligothiophenes (TX(Y)) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells.
The introduction of branching in multi-thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering pi conjugation. Accordingly, branched oligothiophenes require rationalization of their structure reactivity relationships for target-oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T'X-5 of five new multi-thiophene systems, T'5(3), T'8(4), T'11(5), T'14(6), and T'17(7), constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest a-conjugated chain consisting of tri-, tetra-, penta-, hexa-, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5-(2,2'-dithiophene)yl-persubstituted a-oligothiophenes (TXy) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells.
The introduction of branching in multi‐thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering π conjugation. Accordingly, branched oligothiophenes require rationalization of their structure–reactivity relationships for target‐oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T′XY, of five new multi‐thiophene systems, T′53, T′84, T′115, T′146, and T′177, constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest α‐conjugated chain consisting of tri‐, tetra‐, penta‐, hexa‐, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5‐(2,2′‐dithiophene)yl‐persubstituted α‐oligothiophenes (TXY) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells. Branching out: A series of multi‐thiophene systems comprising 5, 8, 11, 14, and 17 thiophene units (an example of which is depicted), their longest α‐conjugated chain consisting of tri‐, tetra‐, penta‐, hexa‐, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view.
The introduction of branching in multi-thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering pi conjugation. Accordingly, branched oligothiophenes require rationalization of their structure-reactivity relationships for target-oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T'X(Y), of five new multi-thiophene systems, T'5(3), T'8(4), T'11(5), T'14(6), and T'17(7), constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest alpha-conjugated chain consisting of tri-, tetra-, penta-, hexa-, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5-(2,2'-dithiophene)yl-persubstituted alpha-oligothiophenes (TX(Y)) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells.
The introduction of branching in multi‐thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering π conjugation. Accordingly, branched oligothiophenes require rationalization of their structure–reactivity relationships for target‐oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T′ X Y , of five new multi‐thiophene systems, T′5 3 , T′8 4 , T′11 5 , T′14 6 , and T′17 7 , constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest α‐conjugated chain consisting of tri‐, tetra‐, penta‐, hexa‐, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5‐(2,2′‐dithiophene)yl‐persubstituted α‐oligothiophenes ( T X Y ) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells.
The introduction of branching in multi-thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular fluxionality and a higher level of distortion, thus hampering pi conjugation. Accordingly, branched oligothiophenes require rationalization of their structure-reactivity relationships for target-oriented design and optimization of the synthetic effort. Our current research on spiderlike oligothiophenes affords deep insight into the subject, and introduces new, easily accessible molecules with attractive functional properties. In particular, a regular series, T'X sub(Y), of five new multi-thiophene systems, T'5 sub(3), T'8 sub(4), T'11 sub(5), T'14 sub(6), and T'17 sub(7), constituted by five, eight, 11, 14, and 17 thiophene units, respectively, their longest alpha -conjugated chain consisting of tri-, tetra-, penta-, hexa-, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view. The electronic properties of the monomers and their electropolymerization ability are discussed and rationalized as a function of their molecular structure, particularly in comparison with the series of 5-(2,2'-dithiophene)yl-persubstituted alpha -oligothiophenes (TX sub(Y)) previously reported by us. These oligothiophenes are easily accessible materials, with promising properties for applications as active layers in multifunctional organic devices including solar cells. Branching out: A series of multi-thiophene systems comprising 5, 8, 11, 14, and 17 thiophene units (an example of which is depicted), their longest alpha -conjugated chain consisting of tri-, tetra-, penta-, hexa-, and heptathiophene moieties, respectively, has been synthesized and fully characterized from the structural, spectroscopic, and electrochemical point of view.
Author Rizzo, Simona
Toffanin, Stefano
Benincori, Tiziana
Mussini, Patrizia R.
Bonometti, Valentina
Falciola, Luigi
Pilati, Tullio
Sannicolò, Francesco
Rampinini, Giovanni
De Angelis, Filippo
Muccini, Michele
Author_xml – sequence: 1
  givenname: Tiziana
  surname: Benincori
  fullname: Benincori, Tiziana
  organization: Dipartimento di Scienze Chimiche ed Ambientali, Università dell'Insubria via Valleggio 11, 22100 Como (Italy)
– sequence: 2
  givenname: Valentina
  surname: Bonometti
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  organization: Dipartimento di Chimica Fisica ed Elettrochimica, Università di Milano via Golgi 19, 20133 Milano (Italy)
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  surname: Pilati
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– sequence: 8
  givenname: Giovanni
  surname: Rampinini
  fullname: Rampinini, Giovanni
  organization: Dipartimento di Chimica Organica e Industriale and C.I.MA.I.NA. Istituto di Scienze e Tecnologie Molecolari, Università di Milano via Venezian 21, 20133 Milano (Italy), Fax: (+39) 02-50314139
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  givenname: Simona
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  givenname: Stefano
  surname: Toffanin
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  givenname: Francesco
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  email: francesco.sannicolo@unimi.it
  organization: Dipartimento di Chimica Organica e Industriale and C.I.MA.I.NA. Istituto di Scienze e Tecnologie Molecolari, Università di Milano via Venezian 21, 20133 Milano (Italy), Fax: (+39) 02-50314139
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Issue 30
Keywords POLYMERS
SERIES
dendrimers
SELENOPHENES
conducting materials
POTENTIALS
MODEL
conjugation
structure-activity relationships
RECOMMENDATIONS
NONAQUEOUS SOLVENTS
ENERGY-TRANSFER
oligothiophenes
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Fondazione Cariplo
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MIUR - No. FIRB-RBNE033KMA
EU Commission - No. FP7/2007-2013
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Snippet The introduction of branching in multi‐thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular...
The introduction of branching in multi-thiophene semiconductors, although granting the required solubility for processing, results in an increased molecular...
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SubjectTerms Accessibility
Branched
Chains
Chemistry
Chemistry, Multidisciplinary
conducting materials
conjugation
dendrimers
Design engineering
oligothiophenes
Physical Sciences
Polymerization
Science & Technology
Semiconductors
Spectroscopy
structure-activity relationships
Thiophenes
Title Towards Molecular Design Rationalization in Branched Multi-Thiophene Semiconductors: The 2-Thienyl-Persubstituted α-Oligothiophenes
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https://www.ncbi.nlm.nih.gov/pubmed/20583047
https://www.proquest.com/docview/1800494297
https://www.proquest.com/docview/748939678
Volume 16
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