Synthesis and Characterization of Near-Infrared Emissive Chiral ­π-Conjugated Polymers Incorporating Perylenyl Moieties with Visible-Light Absorption

Junfeng Li; Ying Chen; Chenglong Yang; Wen-Yong Lai

doi:10.1055/s-0035-1560206

Synlett, Table of Contents

Synlett 2015; 26(17): 2451-2456
DOI: 10.1055/s-0035-1560206

letter

Synthesis and Characterization of Near-Infrared Emissive Chiral π-Conjugated Polymers Incorporating Perylenyl Moieties with Visible-Light Absorption

Junfeng Li*

Key Laboratory for Organic Electronics and Information Displays (KLOEID) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, P. R. of China Email: iamjfli@njupt.edu.cn Email: iamwylai@njupt.edu.cn

,

Ying Chen

Key Laboratory for Organic Electronics and Information Displays (KLOEID) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, P. R. of China Email: iamjfli@njupt.edu.cn Email: iamwylai@njupt.edu.cn

,

Chenglong Yang

Key Laboratory for Organic Electronics and Information Displays (KLOEID) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, P. R. of China Email: iamjfli@njupt.edu.cn Email: iamwylai@njupt.edu.cn

,

Wen-Yong Lai*

Key Laboratory for Organic Electronics and Information Displays (KLOEID) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, P. R. of China Email: iamjfli@njupt.edu.cn Email: iamwylai@njupt.edu.cn

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Abstract

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Abstract

A novel set of multifunctional optically active π-conjugated polymers incorporating perylenyl moieties, were designed and synthesized. Chirality transfer and amplification from chiral unit to the main-chain backbone in dilute solution was achieved, which was closely related to the stereocenter in the pendant of a π-conjugated polymer. In addition, annealed films of these polymers exhibited near-infrared emission by direct absorption of visible light, resulting from the introduction of a strong fluorophore perylenyl moiety. Such a design strategy opens up new perspectives for the future development of novel optically active materials with near-infrared emission for photonic applications.

Key words

π-conjugated polymers - near-infrared emission - visible-light absorption - perylenyl moieties - circular dichroism

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References

References and Notes

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19 Synthesis Procedures for the Perylenyl-Based Chiral Conjugated Polymers Synthesis of P-1 The monomer S-M-1 (46.52 mg, 0.10 mmol), S-M-2 (70.08 mg, 0.10 mmol), Pd(PPh₃)₄ (5.78 mg, 5 mol%), and CuI (1.90 mg, 10 mol%) were added to a mixture of THF (6 mL) and Et₃N (2 mL) in a 20 mL Schlenk tube. The reaction mixture was stirred at 70 °C for 3 d under N₂ atmosphere. After being cooled to r.t., the mixture was filtered through a short silica gel column in MeOH (50 mL) to precipitate the polymer. The solid was filtered and washed with MeOH several times and dried under vacuum to afford 62.06 mg of a dark-red solid in 60% yield. GPC: M _w = 17730; M _n = 9850; PDI = 1.8. [α]_D ²⁵ +460 (c 0.01, THF). ¹H NMR (300 MHz, CDCl₃): δ = 9.44 (d, J = 8.1 Hz), 8.41–8.16 (m), 7.62–7.55 (m), 7.29 (m), 7.26 (m), 4.39 (m), 2.06 (m), 1.81 (m), 1.51 (m), 1.27 (m), 1.02 (m), 0.87 (m) ppm. FT-IR (KBr): 2956, 2929, 2869, 1718, 1276, 1258, 1165, 1063, 1016, 801 cm^–1. Synthesis of P-2 A mixture of THF (6 mL) and Et₃N (2 mL) was repeatedly degassed by purging with nitrogen gas, and then the compound S-M-2 (70.08 mg, 0.10 mmol), S-M-3 (57.58 mg, 0.10 mmol), and CuI (1.90 mg, 10 mol%) along with Pd(PPh₃)₄ (5.78 mg, 5 mol%) were added and refluxed over 3 d under a N₂ atmosphere. After being cooled to r.t., the reaction mixture was filtered through a short silica gel column in MeOH (50 mL) to precipitate out the polymer. The resulting polymer was filtered and washed with MeOH several times and dried under vacuum to afford 62.97 mg of a dark-red solid in 55% yield. GPC: M_w = 14470; M_n = 9120; PDI = 1.6. [α]_D ²⁵ –300 (c 0.01, THF). ¹H NMR (300 MHz, CDCl₃): δ = 9.47 (m), 8.87 (m), 8.62 (m), 8.37–8.28 (m), 7.74–7.41 (m), 6.83 (m), 6.80 (m), 4.38 (s), 2.05 (m), 1.81 (m), 1.53 (m), 1.27 (m), 1.02 (m) ppm. FT-IR (KBr): 2956, 2931, 2870, 1721, 1629, 1455, 1278, 1164, 1063, 1022, 804 cm^–1.

Supplementary Material

Supporting Information

Synthesis and Characterization of Near-Infrared Emissive Chiral ­π-Conjugated Polymers Incorporating Perylenyl Moieties with Visible-Light Absorption

Synthesis and Characterization of Near-Infrared Emissive Chiral π-Conjugated Polymers Incorporating Perylenyl Moieties with Visible-Light Absorption