Supramolecular Organization in Fluorene/Indenofluorene- Oligothiophene Alternating Conjugated Copolymers

Surin, Mathieu; Sonar, Prashant; Grimsdale, Andrew C.; Müllen, Kläus; Lazzaroni, Roberto; Leclère, Ph.

doi:10.1002/adfm.200500241

Cited by 42 publications

(25 citation statements)

References 35 publications

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“…[95][96][97] Modeling studies on the polymer chain packing show that whereas the chains in polymers 17 and 18 have extended linear conformations and can undergo face-to-face packing between the oligothiophene and oligophenylene units to form closely packing ensembles (Figure 2), polymer 16 has a bent lowest energy chain conformation and cannot close-pack in this way. [98] The terthienyl oligomer 19 forms ordered striplike nanostructures when dropcast on glass, mica, or graphite. The height of these stripes (ca.…”

Section: One-dimensional Polyphenylenes and Poly(phenyleneethynylene)smentioning

confidence: 99%

The Chemistry of Organic Nanomaterials

2005

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The development of nanotechnology using organic materials is one of the most intellectually and commercially exciting stories of our times. Advances in synthetic chemistry and in methods for the investigation and manipulation of individual molecules and small ensembles of molecules have produced major advances in the field of organic nanomaterials. The new insights into the optical and electronic properties of molecules obtained by means of single-molecule spectroscopy and scanning probe microscopy have spurred chemists to conceive and make novel molecular and supramolecular designs. Methods have also been sought to exploit the properties of these materials in optoelectronic devices, and prototypes and models for new nanoscale devices have been demonstrated. This Review aims to show how the interaction between synthetic chemistry and spectroscopy has driven the field of organic nanomaterials forward towards the ultimate goal of new technology.

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Section: One-dimensional Polyphenylenes and Poly(phenyleneethynylene)smentioning

confidence: 99%

The Chemistry of Organic Nanomaterials

2005

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“…Besides optical properties, thermal properties, film morphology, and device performance are also dependent on chain length when the molecular weight approaches the macromolecular range 7a. 9–11 Therefore, synthesis of long‐chain MCOs is important for fully exploring the relationship between molecular structure (or length) and properties, as well as for determination of effective conjugation length (ECL), since extrapolating the linear curve of energy gap against the reciprocal of the number of repeating units to estimate the ECL is not reliable for many conjugated systems 2a. 12 However, synthesis of long‐chain MCOs still remains a challenge today, although several series of MCOs with molecular length exceeding 10 nm have been reported 3.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Monodisperse Oligo(fluorene‐co‐bithiophene)s

Zhang

et al. 2007

Chemistry A European J

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A series of monodisperse oligo(9,9-di-n-octylfluorene-co-bithiophene)s (OFbTs) with molecular lengths of up to 19.5 nm and molecular weights up to 7025 g mol(-1) has been synthesized by a divergent/convergent approach involving Stille coupling reactions. Stille coupling is quite efficient in preparing this class of oligomers, and even the molecule with nine fluorene units and eight bithiophene units (F9Th16) can be synthesized in a yield as high as 70 %. Because of easy functionalization of the thiophene ring at its alpha position, no additional protecting group allowing activation for further reaction is necessary. However, the synthetic routes must be optimized to eliminate contamination of the targeting compounds with the homocoupling product of the organotin reagents. Synthesis of the longest oligomer F13Th24 in a relative large quantity is limited by its low yield due to the pronounced ligand-exchange side reactions of the starting materials and reaction intermediates. All oligomers longer than F4Th6 are nematic mesomorphs and exhibit enhanced glass transition temperature and clearing point with increasing molecular length, as revealed by differential scanning calorimetry and polarizing optical microscopy. Absorption and photoluminescence (PL) measurements reveal that OFbTs are well-conjugated systems with an effective conjugation length longer than the length of F13Th24.

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“…The structural features of CPE surfaces are therefore of critical importance to better understand device function and to provide a basis for rational molecular design. Neutral conjugated polymers spontaneously organize from solution upon deposition [9,10] and the degree of order can be influenced by the deposition method, [11] solvent, [12,13] and substrate characteristics. [14] Critical parameters such as charge carrier mobility and emission efficiencies strongly depend on the resulting distance and orientation between the optoelectronic units.…”

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confidence: 99%